m-Chlorophenylacetonitrile → N-{[(1S,2R)-2-{[4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methyl}-1-(3-chlorophenyl)cyclopropyl]methyl}-N-methylbenzenesulfonamide

HRID 2099280Notes

Reaction equation

HRID 2099280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]2([CH2:13][N:14]([CH3:24])[S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:10][C@H:9]2[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(CC#N)C=CC=1.[CH2:35]([C:42]1[N:46]=[C:45]([CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[O:44][N:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([C:42]1[N:46]=[C:45]([CH:47]2[CH2:52][CH2:51][N:50]([CH2:11][C@@H:9]3[CH2:10][C@@:8]3([CH2:13][N:14]([CH3:24])[S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:49][CH2:48]2)[O:44][N:43]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 73722m-ChlorophenylacetonitrileHCID 415417574-(3-Benzyl-1,2,4-oxadiazol-5-yl)piperidineHCID 86603569N-{[(1S,2R)-1-(3-chlorophenyl)-2-formylcyclopropyl]methyl}-N-methylbenzenesulfonamide

Product 1

HCID 57794761N-{[(1S,2R)-2-{[4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methyl}-1-(3-chlorophenyl)cyclopropyl]methyl}-N-methylbenzenesulfonamide

Procedure

N-{[(1S,2R)-1-(3-chlorophenyl)-2-formylcyclopropyl]methyl}-N-methylbenzenesulfonamide [made from (3-chlorophenyl)acetonitrile via the sequential methods of Preparations 1, 2, 3A, 4A, 5A, 6A, 7A, 8A] and 4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidine (incorporating by reference as needed WO 00/39125) were reacted as per Preparation 10 to give the title compound. 1H NMR (300 MHz, CD3OD) δ 7.70-7.53 (m, 5H), 7.36-7.23 (m, 9H), 4.07 (s, 2H), 3.83 (d, J=14.0 Hz, 1H), 3.39-3.16 (m, 4H), 3.09 (d, J=14.0 Hz, 1H), 2.78-2.61 (m, 3H), 2.57 (s, 3H), 2.28-2.21 (m, 2H), 2.07-1.94 (m, 2H), 1.53-1.48 (m, 1H), 1.33-1.29 (m, 1H), 1.00-0.96 (m, 1H). ES-LCMS m/z 591.5 (M+H).

Workup

  1. customwere reacted as per Preparation 10

Sources & evidence

ORD record
ord-7a02cec4bf834513b2b0a511754b7d72
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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