Dimethylamine → HCID 59421009, compound

HRID 1257931Notes

Reaction equation

HRID 1257931 reaction equation
[CH:1]([N:4](CC)[CH:5](C)C)(C)C.[F:10][C:11]1[CH:24]=[C:23]([C:25]2[CH:26]=[N:27][C:28]3[N:29]([C:31]([C:34]4([C:37]5[CH:38]=[C:39]6[C:44](=[CH:45][CH:46]=5)[N:43]=[CH:42][CH:41]=[CH:40]6)[CH2:36][CH2:35]4)=[CH:32][N:33]=3)[CH:30]=2)[CH:22]=[CH:21][C:12]=1[C:13]([NH:15][CH:16]([CH3:20])[C:17]([OH:19])=O)=[O:14].CNC.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>[CH3:1][N:4]([CH3:5])[C:17](=[O:19])[CH:16]([NH:15][C:13](=[O:14])[C:12]1[CH:21]=[CH:22][C:23]([C:25]2[CH:26]=[N:27][C:28]3[N:29]([C:31]([C:34]4([C:37]5[CH:38]=[C:39]6[C:44](=[CH:45][CH:46]=5)[N:43]=[CH:42][CH:41]=[CH:40]6)[CH2:35][CH2:36]4)=[CH:32][N:33]=3)[CH:30]=2)=[CH:24][C:11]=1[F:10])[CH3:20]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67224078HCID 67224078, compound

Product 1

HCID 59421009HCID 59421009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (31 μL, 0.18 mmol) was added to a mixture of 2-(2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoylamino)propanoic acid (29.7 mg, 0.06 mmol), dimethylamine (4.0 mg, 0.09 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (40 mg, 0.09 mmol) in N,N-dimethylformamide (0.5 mL). The reaction mixture was stirred overnight at RT and purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=523.1.

Workup

  1. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-ead2fe4deb5540e7b054601217080bb6
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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