(3'S,4'R,7'S,8'S,8a'R)-6''-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3''-pyrrolo[2,3-b]pyridine]-1',2''(1''H)-dione → HCID 178423624, compound

HRID 470663Notes

Reaction equation

HRID 470663 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:47])[C@:10]3([C:18]4([CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]4)[N:17]4[C@@H:12]([C:13](=[O:38])[O:14][C@@H:15]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C@H:16]4[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:11]3[C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=3[F:46])[C:5]2=[CH:4][CH:3]=1.[NH2:48][C@H:49]1[CH2:54][CH2:53][C@H:52]([CH2:55][OH:56])[CH2:51][CH2:50]1>>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:47])[C:10]3([C@@H:11]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=4[F:46])[C@H:12]([C:13]([NH:48][C@H:49]4[CH2:54][CH2:53][C@H:52]([CH2:55][OH:56])[CH2:51][CH2:50]4)=[O:38])[N:17]([C@H:16]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:15]([OH:14])[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:18]43[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]4)[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86672583(3'S,4'R,7'S,8'S,8a'R)-6''-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3''-pyrrolo[2,3-b]pyridine]-1',2''(1''H)-dioneHCID 178511560HCID 178511560, compound

Product 1

HCID 178423624HCID 178423624, compoundYield 83.4%

Procedure

The compound (260 mg, 0.39 mmol) obtained in Step 1 above and (trans-4-aminocyclohexyl)methanol (100 mg, 0.77 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 1 to give 260 mg (83%) of the title compound as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-af662f47bb524c0c88ee85523a849c1d
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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