Dimethylamine → HCID 86714677, compound

HRID 1409469Notes

Reaction equation

HRID 1409469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:35]([OH:37])=O)[N:25]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:26]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9].[CH3:38][NH:39][CH3:40]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:35]([N:39]([CH3:40])[CH3:38])=[O:37])[N:25]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:32])[CH3:33])[CH:26]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 86714676HCID 86714676, compound

Product 1

HCID 86714677HCID 86714677, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from (S)-4-((1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)carbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acid (0.549 mmol, 300 mg) and N,N-dimethylamine (0.824 mmol, 37 mg). The product was purified by flash-chromatography. Yield 207 mg. 1H-NMR (400 MHz; CDCl3): δ −0.01 (s, 9H), 0.91 (t, 2H), 1.26 (d, 3H), 3.11 (s, 3H), 3.26 (s, 3H), 3.54 (t, 2H), 4.31-4.42 (m, 2H), 4.51-4.57 (m, 1H), 5.74 (s, 2H), 6.59 (d, 1H), 7.39 (d, 1H), 7.49 (d, 1H), 7.59 (d, 1H), 7.81 (s, 1H), 7.84 (s, 1H). LC-MS: [M+1]=574.32.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-76a9c2e0654a41e6a8105d15d40e621f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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