Diisopropylethylamine → HCID 59420963, compound

HRID 1257899Notes

Reaction equation

HRID 1257899 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][C:14]3[N:15]([C:17]([C:20]4([C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[CH:28][CH:27]=[CH:26]6)[CH2:22][CH2:21]4)=[CH:18][N:19]=3)[CH:16]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:33][O:34][CH2:35][CH:36]([NH2:38])[CH3:37].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][C:14]3[N:15]([C:17]([C:20]4([C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[CH:28][CH:27]=[CH:26]6)[CH2:22][CH2:21]4)=[CH:18][N:19]=3)[CH:16]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:38][CH:36]([CH3:37])[CH2:35][O:34][CH3:33])=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 123458MethoxyisopropylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67225308HCID 67225308, compound

Product 1

HCID 59420963HCID 59420963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid (19 mg, 0.045 mmol), 1-methoxypropan-2-amine (8 mg, 0.090 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (40 mg, 0.090 mmol), and N,N-diisopropylethylamine (31 μL, 0.18 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at RT for 2 h. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=496.1

Workup

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

Sources & evidence

ORD record
ord-b85bbbc8e2ad4504904b7d1af0ec4275
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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