Sodium hydride → HCID 178422600, compound

HRID 1898427Notes

Reaction equation

HRID 1898427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[N:7][OH:8])[NH2:6].[H-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[NH:23][C:24]1[NH:28][C:27]2[C:29]3[CH2:30][C:31]([CH3:41])([CH3:40])[O:32][C:33]=3[C:34]([C:36](OC)=O)=[CH:35][C:26]=2[N:25]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:36]([C:34]3[C:33]4[O:32][C:31]([CH3:41])([CH3:40])[CH2:30][C:29]=4[C:27]4[NH:28][C:24]([NH:23][C:17]5[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=5[Cl:15])=[N:25][C:26]=4[CH:35]=3)[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 44117393-chloro-4-fluoro-N-hydroxy-benzenecarboximidamideHCID 178496985HCID 178496985, compound

Product 1

HCID 178422600HCID 178422600, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-156 using 3-chloro-4-fluoro-N′-hydroxybenzimidamide (Intermediate-53, 0.072 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 (5.0 mL) to afford 0.029 g of the desired product. 1HNMR (DMSO-d6): δ 1.33 (s, 6H), 3.08 (s, 2H), 7.26 (bs, 1H), 7.55 (m, 3H), 7.65 (t, J=8.7 Hz, 1H), 8.06 (s, 1H), 8.06 (s, 1H), 8.16 (d, J=5.7 Hz, 1H), 11 (bs, 2H); MS [M+H]+: 544.17.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0175b53bb0d54cb2b136227142f72ed6
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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