Sodium hydride → HCID 86662208, compound

HRID 1467852Notes

Reaction equation

HRID 1467852 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][CH:34]3[CH2:37][CH2:36][CH2:35]3)=[C:27]([Cl:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:16][C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH:26]=[C:27]([Cl:38])[C:28]([O:32][CH2:33][CH:34]5[CH2:37][CH2:36][CH2:35]5)=[C:29]([Cl:31])[CH:30]=4)[N:24]=3)=[O:18])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662209HCID 86662209, compound

Product 1

HCID 86662208HCID 86662208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (45 mg, 0.251 mmol) with 2-bromo-N-{4-[4-(cyclobutylmethoxy)-3,5-dichlorophenyl]-1,3-thiazol-2-yl}acetamide (135 mg, 0.301 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 65 mg of the product as an off-white solid; 1H NMR ((δ ppm, 300 MHz, DMSO-d6) 1.90-1.99 (m, 4H), 2.04-2.10 (m, 2H), 2.72-2.80 (m, 1H), 3.17 (s, 3H), 3.39 (s, 3H), 4.00 (d, J=6.3 Hz, 2H), 5.32 (s, 2H), 6.22 (s, 1H), 7.36 (s, 1H), 7.85 (s, 1H), 8.00 (s, 2H), 12.68 (br s, 1H); ESI-MS (m/z) 548.15 (M+H)+.

Sources & evidence

ORD record
ord-fafe0c6eca164d759c306adb5b002881
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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