Sodium hydride → HCID 178493443, compound

HRID 1898428Notes

Reaction equation

HRID 1898428 reaction equation
[OH:1][N:2]=[C:3]([NH2:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[CH:5]=1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[NH:25][C:26]1[NH:30][C:29]2[C:31]3[CH2:32][C:33]([CH3:43])([CH3:42])[O:34][C:35]=3[C:36]([C:38](OC)=O)=[CH:37][C:28]=2[N:27]=1>C1COCC1>[Cl:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[C:19]=1[NH:25][C:26]1[NH:30][C:29]2[C:31]3[CH2:32][C:33]([CH3:43])([CH3:42])[O:34][C:35]=3[C:36]([C:38]3[O:1][N:2]=[C:3]([C:4]4[CH:5]=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=4)[N:14]=3)=[CH:37][C:28]=2[N:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2731154Benzenecarboximidamide, N-hydroxy-3,5-dimethoxy-HCID 178496985HCID 178496985, compound

Product 1

HCID 178493443HCID 178493443, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-156 using N′-hydroxy-3,5-dimethoxybenzimidamide (Intermediate-54, 0.075 g, 0.30 mmol), sodium hydride (0.021 g, 0.51 mmol), methyl 2-((2-chloro-6-chlorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Step-1 of Intermediate-6, 0.100 g, 0.255 mmol) and THF to afford 0.029 g of the desired product. 1HNMR (DMSO-d6): δ 1.29 (d, J=7.8 Hz, 6H), 3.09 (s, 2H), 3.85 (s, 6H), 6.58 (s, 1H), 7.30 (m, 3H), 7.44 (d, 1H), 7.78 (s, 1H). MS [M+H]+: 552.09.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3316e77e74e349a68d72e20c7028cb6e
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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