(3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-3,3-bis(fluoromethyl)-2''-oxo-1'',2''-dihydrodispiro[cyclobutane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxylic acid → HCID 178484573, compound

HRID 470679Notes

Reaction equation

HRID 470679 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][CH:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24](O)=[O:25])[NH:13][C:12]43[CH2:29][C:28]([CH2:32][F:33])([CH2:30][F:31])[CH2:27]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.Cl.[NH2:35][C@H:36]1[CH2:41][CH2:40][C@H:39]([C:42]([N:44]([CH3:46])[CH3:45])=[O:43])[CH2:38][CH2:37]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][CH:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24]([NH:35][C@H:36]4[CH2:37][CH2:38][C@H:39]([C:42](=[O:43])[N:44]([CH3:45])[CH3:46])[CH2:40][CH2:41]4)=[O:25])[NH:13][C:12]43[CH2:27][C:28]([CH2:30][F:31])([CH2:32][F:33])[CH2:29]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 70871764(3'R,4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-3,3-bis(fluoromethyl)-2''-oxo-1'',2''-dihydrodispiro[cyclobutane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxylic acidHCID 178484570HCID 178484570, compound

Product 1

HCID 178484573HCID 178484573, compoundYield 68%

Procedure

The compound (70 mg, 0.14 mmol) obtained in Step 1 of Example 121 and trans-4-amino-N,N-dimethylcyclohexanecarboxamide hydrochloride (WO2008/068171) (29 mg, 0.17 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 12 to give 62 mg (68%) of the title compound as a colorless amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-68cbfabffb704a5cac54a22b9cbe8ce2
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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