Sodium hydride → HCID 46947435, compound

HRID 1467841Notes

Reaction equation

HRID 1467841 reaction equation
[CH3:1][N:2]1[C:7]2[C:8](C)=[CH:9][NH:10][C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].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][CH2:34][CH:35]([CH3:37])[CH3:36])=[C:27]([F:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(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:10]3[C:6]4[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:7]=4[CH:8]=[CH:9]3)[S:21][CH:22]=2)[CH:30]=[C:29]([F:31])[C:28]=1[O:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662189HCID 86662189, compound

Product 1

HCID 46947435HCID 46947435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (50 mg, 0.279 mmol) with 2-bromo-N-{4-[3,5-difluoro-4-(3-methylbutoxy)phenyl]-1,3-thiazol-2-yl}acetamide (140 mg, 0.334 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 75 mg of the product as an off-white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 0.92 (d, J=6.6 Hz, 6H), 1.60 (d, J=6.3 Hz, 2H), 1.75-1.85 (m, 1H), 3.17 (s, 3H), 3.39 (s, 3H), 4.15 (d, J=6.3 Hz, 2H), 5.32 (s, 2H), 6.22 (s, 1H), 7.35 (s, 1H), 7.63 (s, 1H), 7.66 (s, 1H), 7.77 (s, 1H), 12.68 (br s, 1H); ESI-MS (m/z) 516.41 [M−H].

Sources & evidence

ORD record
ord-b4b2f7a5393f4089b5d6c5c12fb2c5c9
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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