Ethyl 4-oxocyclohexanecarboxylate → (S)-4-(5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-cyclohexanecarboxylic acid ethyl ester

HRID 507173Notes

Reaction equation

HRID 507173 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([C@H:14]1[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:16]2[CH:27]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:29]([CH3:31])=[CH:30][C:15]1=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH2:45]([O:47][C:48](C1CCC(=O)CC1)=[O:49])[CH3:46]>>[CH2:45]([O:47][C:48]([CH:25]1[CH2:26][CH2:22][CH:21]([N:17]2[CH2:18][CH2:19][CH2:20][C@H:14]([N:7]([CH2:6][C:5]3[CH:36]=[C:37]([C:39]([F:42])([F:40])[F:41])[CH:38]=[C:3]([C:2]([F:43])([F:1])[F:44])[CH:4]=3)[C:8]3[N:9]=[N:10][N:11]([CH3:13])[N:12]=3)[C:15]3[CH:30]=[C:29]([CH3:31])[C:28]([C:32]([F:33])([F:34])[F:35])=[CH:27][C:16]2=3)[CH2:23][CH2:24]1)=[O:49])[CH3:46]

Participants

3

Reactant 2

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 11505545(S)-(3,5-Bistrifluoromethylbenzyl)-(1-cyclopentylmethyl-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)amine

Product 1

HCID 59432485(S)-4-(5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-cyclohexanecarboxylic acid ethyl ester

Procedure

Prepare the title compound by essentially following the procedures described in the synthesis of (S)-(3,5-Bistrifluoromethylbenzyl)-(1-cyclopentylmethyl-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)amine (Example 3 step 19) by replacing cyclopentanecarboxaldehyde with 4-oxo-cyclohexanecarboxylic acid ethyl ester. Isolate the title compound by chromatography over silica gel, eluting with ethyl acetate/hexane. MS (ES+): 707 (M+H).

Sources & evidence

ORD record
ord-8d0b19051ac146b28b336aac89801cc7
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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