Dimethylformamide → HCID 46947244, compound

HRID 1467855Notes

Reaction equation

HRID 1467855 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]=[C:29]([F:31])[C:28]([O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([F:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+].[CH3:41]N(C=O)C>>[F:38][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]([CH3:41])=[CH:1]3)[S:21][CH:22]=2)[CH:30]=[C:29]([F:31])[C:28]=1[O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 86662190HCID 86662190, compoundHCID 178434372HCID 178434372, compound

Product 1

HCID 46947244HCID 46947244, 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-[3,5-difluoro-4-(2,2-dimethylpropoxy)phenyl]-1,3-thiazol-2-yl}acetamide (130 mg, 0.310 mmol) in the presence of NaH (15 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 75 mg of the product as a white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz) 1.01 (s, 9H), 2.29 (s, 3H), 3.16 (s, 3H), 3.59 (s, 3H), 3.80 (s, 2H), 5.25 (s, 2H), 7.12 (s, 1H), 7.63 (d, J=9.6 Hz, 2H), 7.76 (s, 1H), 12.63 (br s, 1H, exchangeable with D2O); ESI-MS (m/z) 532.18 (M+H)+.

Sources & evidence

ORD record
ord-ad4bf7385f6c4fc58516c87cd0d70ac8
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

Loading…