1-Methyl-5-aminomethylimidazole → (3'R,4'S,5'R)-6''-chloro-4'-(2-chloro-3-fluoropyridin-4-yl)-4,4-dimethyl-N-[(1-methyl-1H-imidazol-5-yl)methyl]-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamide

HRID 470681Notes

Reaction equation

HRID 470681 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([C@@H:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24]([OH:26])=O)[NH:13][C:12]43[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][CH2:27]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:34][N:35]1[C:39]([CH2:40][NH2:41])=[CH:38][N:37]=[CH:36]1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C@@H:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24]([NH:41][CH2:40][C:39]4[N:35]([CH3:34])[CH:36]=[N:37][CH:38]=4)=[O:26])[NH:13][C:12]43[CH2:31][CH2:30][C:29]([CH3:32])([CH3:33])[CH2:28][CH2:27]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27954241-Methyl-5-aminomethylimidazoleHCID 86672588HCID 86672588, compound

Product 1

HCID 86672594(3'R,4'S,5'R)-6''-chloro-4'-(2-chloro-3-fluoropyridin-4-yl)-4,4-dimethyl-N-[(1-methyl-1H-imidazol-5-yl)methyl]-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamideYield 41%

Procedure

The compound (400 mg, 0.81 mmol) obtained in Step 1 of Example 17 and 1-(1-methyl-1H-imidazole-5-yl)methanamine (95 mg, 0.98 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 12 to give 188 mg (41%) of the title compound as a solid.

Workup

  1. additiontreated in the same way as in Step 2 of Example 12

Sources & evidence

ORD record
ord-7e380f1c067b4485a47fab1727ac7092
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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