Sodium hydride → HCID 86662200, compound

HRID 1467848Notes

Reaction equation

HRID 1467848 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]([Cl:31])[C:28]([O:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])=[C:27]([Cl:42])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[Cl:42][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]([Cl:31])[C:28]=1[O:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:38])([F:39])[F:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662201HCID 86662201, compound

Product 1

HCID 86662200HCID 86662200, 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-dichloro-4-(3,3,4,4,4-pentafluorobutoxy)phenyl]-1,3-thiazol-2-yl}acetamide (176 mg, 0.332 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 58 mg of the product as an off-white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 2.80-2.86 (m, 2H), 3.17 (s, 3H), 3.39 (s, 3H), 4.25-4.32 (m, 2H), 5.32 (s, 2H), 6.23 (s, 1H), 7.35 (s, 1H), 7.88 (s, 1H), 8.03 (s, 2H), 12.70 (br s, 1H); ESI-MS (m/z) 626.18 (M+H)+.

Sources & evidence

ORD record
ord-784bc435f27e40f8adbdc94999cff695
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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