Diisopropylethylamine → 1'-(3-(S)-(4-Chlorophenyl)-4-(N-(3,5-bistrifluoromethylbenzoyl)-(methylamino))butyl)-spiro(2,3-dihydrobenzothiophene-3,4'-piperidine)

HRID 1737438Notes

Reaction equation

HRID 1737438 reaction equation
Br[CH2:2][CH2:3][C@@H:4]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:5][N:6]([CH3:23])[C:7](=[O:22])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1.Cl.[NH:32]1[CH2:37][CH2:36][C:35]2([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[S:39][CH2:38]2)[CH2:34][CH2:33]1.C(N(C(C)C)CC)(C)C>>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C@@H:4]([CH2:5][N:6]([CH3:23])[C:7](=[O:22])[C:8]2[CH:9]=[C:10]([C:18]([F:19])([F:20])[F:21])[CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[CH:13]=2)[CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][C:35]3([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=4[S:39][CH2:38]3)[CH2:34][CH2:33]2)=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 70028544Spiro(benzo[b] thiophene-3(2H),4'-piperidine) hydrochlorideHCID 867545684-bromo-2-(S)-(4-chlorophenyl)-1-(N-(3,5-bistrifluoromethylbenzoyl)-methylamino)butane

Product 1

HCID 183927041'-(3-(S)-(4-Chlorophenyl)-4-(N-(3,5-bistrifluoromethylbenzoyl)-(methylamino))butyl)-spiro(2,3-dihydrobenzothiophene-3,4'-piperidine)

Procedure

The title compound was prepared as in Example 21 from 4-bromo-2-(S)-(4-chlorophenyl)-1-(N-(3,5-bistrifluoromethylbenzoyl)-methylamino)butane and spiro(2,3-dihydrobenzothiophene-3,4'-piperidine) hydrochloride except that 3 eq. of diisopropylethylamine were used.

Sources & evidence

ORD record
ord-5aeff29a18c8455bb22616d6cc25140c
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

Loading…