Dimethylformamide → HCID 46945049, compound

HRID 1467856Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[N:7]([CH3:14])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=2[NH:4]N=1.Br[CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[C:27]([F:35])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+].[CH3:38]N(C=O)C>>[F:35][C:27]1[CH:26]=[C:25]([C:23]2[N:24]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][N:4]3[C:5]4[C:10](=[O:11])[N:9]([CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=4[C:2]([CH3:38])=[CH:1]3)[S:21][CH:22]=2)[CH:30]=[CH:29][C:28]=1[C:31]([F:34])([F:33])[F:32]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 86662184HCID 86662184, compound

HCID 178434372HCID 178434372, compound

Product 1

HCID 46945049HCID 46945049, compound

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 3 (50 mg, 0.258 mmol) with 2-bromo-N-{4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide (119 mg, 0.310 mmol) in the presence of NaH (15 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 90 mg of the product as a white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz) 2.29 (s, 3H), 3.16 (s, 3H), 3.59 (s, 3H), 5.26 (s, 2H), 7.12 (s, 1H), 7.82-8.00 (m, 4H), 12.71 (br s, 1H, exchangeable with D2O); APCI-MS (m/z) 494.30 (M−H)−.

Sources & evidence

ORD record: ord-e8846aa3cfe84793b3f8c516aec1c79a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000159B2

Reaction notes

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