Diisopropylethylamine → HCID 59173275, compound

HRID 220098Notes

Reaction equation

HRID 220098 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9]2[N:13]([C:14]3[CH:19]=[C:18]([NH:20][CH3:21])[N:17]=[CH:16][N:15]=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)=[CH:6][C:5]([NH2:23])=[CH:4][CH:3]=1.[CH:24]([NH:27][CH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[C:32](O)=[O:33])([CH3:26])[CH3:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:24]([NH:27][CH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:37]=1)[C:32]([NH:23][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([NH:8][C:9]2[N:13]([C:14]3[CH:19]=[C:18]([NH:20][CH3:21])[N:17]=[CH:16][N:15]=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)[CH:6]=1)=[O:33])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59173317HCID 59173317, compoundHCID 59173398HCID 59173398, compound

Product 1

HCID 59173275HCID 59173275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-N1-(3-methyl-1-(6-(methylamino)pyrimidin-4-yl)-1H-pyrazol-5-yl)benzene-1,3-diamine 39 (360 mg, 1.16 mmol, 1 eq) is dissolved in dry DMF (10 mL), followed by 3-((isopropylamino)methyl)-5-(trifluoromethyl)benzoic acid (0.504 mg, 1.02 mmol, 0.9 eq), HATU (663 mg, 1.74 mmol, 1.5 eq), and DIEA (0.5 mL, 3.49 mmol, 3 eq). The reaction mixture is stirred at room temperature for about 4 hours until the reaction is complete as evidenced by the LC/MS product peak. The reaction mixture is then quenched by NaHCO3 solution and extracted with ethyl acetate. The organic layers are combined and dried over magnesium sulfate. The solvents are removed under vacuo and the residue is purified by flash column chromatography to afford 3-((isopropylamino)methyl)-N-(4-methyl-3-(3-methyl-1-(6-(methylamino)pyrimidin-4-yl)-1H-pyrazol-5-ylamino)phenyl)-5-(trifluoromethyl)benzamide. MS: m/z [M+H+]) 553.20, 1H NMR: 11.07 (s, 1H), 10.61 (s, 1H), 9.17 (bs, 1H), 8.58 (s, 1H), 8.45 (s, 1H), 8.35 (s, 1H), 8.21 (s, 1H), 7.95 (s, 1H), 7.69 (s, 1H), 7.39 (m, 1H), 7.24 (m, 1H), 6.88 (s, 1H), 6.16 (s, 1H), 4.36 (m, 2H), 3.34-3.48 (m, 1H), 2.87 (m, 3H), 2.49 (m, 3H), 2.22 (m, 3H), 1.33-1.34 (m, 6H).

Workup

  1. customThe reaction mixture is then quenched by NaHCO3 solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents are removed under vacuo
  5. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-1535b3d1b20a47739ad015218924453c
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

Loading…