4-(Trifluoromethoxy)benzylamine → HCID 67479167, compound

HRID 1019655Notes

Reaction equation

HRID 1019655 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][CH2:23][C@H:22]([C:26]([OH:28])=O)[CH2:21]4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:53][C:54]([F:65])([F:64])[O:55][C:56]1[CH:63]=[CH:62][C:59]([CH2:60][NH2:61])=[CH:58][CH:57]=1>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][CH2:23][C@H:22]([C:26]([NH:61][CH2:60][C:59]5[CH:62]=[CH:63][C:56]([O:55][C:54]([F:53])([F:64])[F:65])=[CH:57][CH:58]=5)=[O:28])[CH2:21]4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67479226HCID 67479226, compound

Product 1

HCID 67479167HCID 67479167, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.3 (491 mg, 1.280 mmol) and TEA (535 μL, 3.84 mmol) in DCM (6402 μL) was added HATU (536 mg, 1.409 mmol) followed by 4-(trifluoromethoxy)benzylamine (Apollo Scientific Ltd., 215 μL 1.409 mmol) The reaction was stirred at room temperature for 40 hours. The reaction then was concentrated and the residue was adsorbed onto a plug of silica gel and purified by chromatography through a 50 g silica gel column, eluting with 0.5 to 5% MeOH in DCM, to provide 3 as a light purple solid in 23% yield. 1H NMR (300 MHz, CD3OD) δ ppm 1.62 (br. s., 1H) 1.79-1.93 (m, 2H) 1.93-2.10 (m, 1H) 2.54 (br. s., 1H) 3.12 (br. s., 4H) 3.35-3.52 (m, 2H) 3.81 (br. s., 4H) 4.22-4.37 (m, 4H) 6.45 (d, J=7.31 Hz, 1H) 6.99 (d, J=8.62 Hz, 2H) 7.21 (d, J=8.04 Hz, 2H) 7.33 (t, J=8.40 Hz, 4H) 7.65 (d, J=7.31 Hz, 1H); M+H 557.24764.

Workup

  1. customThe reaction
  2. concentrationthen was concentrated
  3. custompurified by chromatography through a 50 g silica gel column
  4. washeluting with 0.5 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-18bbe930e17b4ce682cc6835c19cd0fe
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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