Methylamine → HCID 59421003, compound

HRID 1257903Notes

Reaction equation

HRID 1257903 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:19]=[C:18]([C:20]2[CH:21]=[N:22][C:23]3[N:24]([C:26]([C:29]4([C:32]5[CH:33]=[C:34]6[C:39](=[CH:40][CH:41]=5)[N:38]=[CH:37][CH:36]=[CH:35]6)[CH2:31][CH2:30]4)=[CH:27][N:28]=3)[CH:25]=2)[CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14].CN.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:10][C:11]1[CH:19]=[C:18]([C:20]2[CH:21]=[N:22][C:23]3[N:24]([C:26]([C:29]4([C:32]5[CH:33]=[C:34]6[C:39](=[CH:40][CH:41]=5)[N:38]=[CH:37][CH:36]=[CH:35]6)[CH2:31][CH2:30]4)=[CH:27][N:28]=3)[CH:25]=2)[CH:17]=[CH:16][C:12]=1[C:13]([NH:4][CH3:1])=[O:14]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67224685HCID 67224685, compound

Product 1

HCID 59421003HCID 59421003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (14 μL, 0.081 mmol) was added to a mixture of 2-chloro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid (0.027 mmol), methylamine (2M in THF, 0.2 mL, 0.4 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (14 mg, 0.032 mmol) in N,N-dimethylformamide (0.5 mL). The mixture was stirred at RT for 2 h, and then purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=454.1/456.0.

Workup

  1. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-870bf67707db4d8fbcf7d750c3152579
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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