Methylamine → 2,3-difluoro-N-methyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzamide

HRID 500268Notes

Reaction equation

HRID 500268 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:18]([C:21]4([C:24]5[CH:25]=[C:26]6[C:31](=[CH:32][CH:33]=5)[N:30]=[CH:29][CH:28]=[CH:27]6)[CH2:23][CH2:22]4)=[CH:19][N:20]=3)[CH:17]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN.F[P-](F)(F)(F)(F)F.[N:43]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:47]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:18]([C:21]4([C:24]5[CH:25]=[C:26]6[C:31](=[CH:32][CH:33]=5)[N:30]=[CH:29][CH:28]=[CH:27]6)[CH2:23][CH2:22]4)=[CH:19][N:20]=3)[CH:17]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:43][CH3:47])=[O:6]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 672248992,3-Difluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid

Product 1

HCID 594209402,3-difluoro-N-methyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-difluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid (9.0 mg, 0.020 mmol), methylamine (2M in THF, 0.02 mL, 0.041 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (11 mg, 0.024 mmol) and N,N-diisopropylethylamine (11 μL, 0.061 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at RT for 4 h. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=456.0.

Workup

  1. customThe reaction mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-bdc2764f5dcc45e0a37db9bb24cb52e6
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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