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Ammonium Chloride → tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate

HRID 2272408
Notes
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Reaction equation

HRID 2272408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[C:25]([CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH2:35][C:36]([O-:38])=O)[C:24]([C:39]([F:42])([F:41])[F:40])=[CH:23][N:22]=3)=[C:16]([O:43][CH3:44])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[N:47](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:47][C:36](=[O:38])[CH2:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][CH2:27][C:25]1[C:24]([C:39]([F:40])([F:42])[F:41])=[CH:23][N:22]=[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]3)=[CH:15][C:16]=2[O:43][CH3:44])[N:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68283397Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

Product 1

HCID 68283338
tert-Butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (I22) (210 mg, 0.338 mmol), HATU (257 mg, 0.676 mmol), ammonium chloride (362 mg, 6.76 mmol) and DIPEA (115 μL) in dry DMF (4 mL) was stirred at room temperature overnight. The volatiles were evaporated under reduced pressure and the residue diluted with ethyl acetate. The resulting solution was washed with 10% NaHCO3 then the organic layer dried (MgSO4). The volatiles were removed under reduced pressure and the residue chromatographed (SiO2, 0-100% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I23) (185 mg, 89%) as a colourless solid; 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.26 (d, J=8.3 Hz, 1H), 7.88 (s, 1H), 7.25 (dd, J=4.4, 2.4 Hz, 2H), 6.86 (dd, J=8.3, 1.7 Hz, 1H), 6.76 (d, J=1.7 Hz, 1H), 5.49 (d, J=39.2 Hz, 2H), 4.24 (s, 2H), 3.92 (s, 3H), 3.70 (s, 2H), 3.20-3.02 (m, 4H), 2.80 (m, 2H), 2.64 (s, 2H), 1.84 (d, J=12.8 Hz, 2H), 1.62 (dd, J=12.3, 3.5 Hz, 2H), 1.49 (s, 9H). LCMS Method C: rt 6.64 min; m/z 636.2 [M+Na]+, 614.1 [M+1]+, 612.2 [M−1]−, 558.2 [M-t-Bu+2]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. additionthe residue diluted with ethyl acetate
  3. washThe resulting solution was washed with 10% NaHCO3
  4. dry with materialthe organic layer dried (MgSO4)
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue chromatographed (SiO2, 0-100% ethyl acetate/petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-3f2c2eb883424e6297acf46bf74b0981
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120761B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes