Diisopropylethylamine → HCID 58797866, compound

HRID 2220498Notes

Reaction equation

HRID 2220498 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([C@H:18]1[C:25]2[CH:24]=[N:23][N:22]([CH3:26])[C:21]=2[CH2:20][NH:19]1)=[O:17].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36](O)=[O:37])[CH:34]=2)[CH:29]=[CH:28]1.CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([C@H:18]1[C:25]2[CH:24]=[N:23][N:22]([CH3:26])[C:21]=2[CH2:20][N:19]1[C:36]([C:33]1[CH:34]=[C:35]2[C:30]([CH:29]=[CH:28][NH:27]2)=[CH:31][CH:32]=1)=[O:37])=[O:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 5952301H-indole-6-carboxylic acidHCID 69447078HCID 69447078, compound

Product 1

HCID 58797866HCID 58797866, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)-1-methyl-1,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazole-4-carboxylic acid [2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide (example 1B), 38 mg), 6-indolecarboxylic acid (22 mg), 0.03 ml (DIPEA) and BOPCl (51 mg) in 2 ml acetonitrile was stirred for 2 hrs at 0° C. A consecutive basic and acidic work up delivered a yellow oil which was purified by chromatography (silica gel, AcOEt). (R)-5-(1H-Indole-6-carbonyl)-1-methyl-1,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazole-4-carboxylic acid [2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide was obtained as a white solid (13 mg). MS: 497.0 (M+H)+

Workup

  1. customwas purified by chromatography (silica gel, AcOEt)

Sources & evidence

ORD record
ord-34047a19725a4cca9ca2438d3050d8ef
Source dataset
uspto-grants-2008_08
Patent number
US07417144B2

Reaction notes

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