2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → HCID 136342128, compound

HRID 748544Notes

Reaction equation

HRID 748544 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[Cl:13][C:14]1[N:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[ClH:13].[OH:12][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:23]3[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]3)(=[O:22])=[O:21])=[CH:18][N:19]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

Participants

3

Reactant 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 43421737HCID 43421737, compound

Product 1

HCID 136342128HCID 136342128, compoundYield 30%

Procedure

The title compound was prepared as described for Example 82 using 5-cyanooxindole and 1-[(6-chloropyridin-3-yl)sulfonyl]-4-isopropylpiperazine. Yield: 30% of the title compound as a yellow solid; 1H NMR (DMSO-d6, 400 MHz) δ 11.56 (br s, 1 H), 10.68 (br s, 1 H), 8.57 (br s, 1 H), 8.02 (s, 1 H), 7.93-7.81 (m, 1 H), 7.74 (dd, J=9, 2 Hz, 1 H), 7.42 (dd, J=8, 1 Hz, 1 H), 7.06 (d, J=8 Hz, 1 H) 3.82-3.71 (m, 2 H), 3.58-3.31 (m, 3 H), 3.24-1.82 (m, 4 H), 1.24 (d, J=7 Hz, 6 H); MS (ES) m/z 304 (M++1).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8e3d4b5f9f804826bb51ca1cfad1de6a
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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