HCID 89893838, compound → HCID 72195746, compound

HRID 1486826Notes

Reaction equation

HRID 1486826 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[C:12]3[C:32]([C:36]#[C:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:33][CH:34]=[N:35][C:11]2=3)(=O)=O)C=CC=CC=1>CO>[CH3:31][N:28]1[CH2:27][CH2:26][N:25]([C:22]2[CH:21]=[CH:20][C:19]([C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[NH:10][C:11]3[N:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:12]4=3)=[CH:24][CH:23]=2)[CH2:30][CH2:29]1

Participants

3

Reactant 1

HCID 89893838HCID 89893838, compound

Product 1

HCID 72195746HCID 72195746, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9-Benzenesulfonyl-6-[4-(4-methylpiperazin-1-yl)-phenyl]-4-phenylethynyl-9H-pyrido[2,3-b]indole underwent typical procedure A. The trituration procedure in MeOH afforded the desired compound in 81% yield as a brown solid. 1H-NMR (300 MHz, DMSO) δ=12.07 (s, 1H), 8.69 (d, J=2.2 Hz, 1H), 8.46 (d, J=5.1 Hz, 1H), 7.82-7.74 (m, 3H), 7.63-7.54 (m, 6H), 7.34 (d, J=5.1 Hz, 1H), 7.04 (d, J=8.7 Hz, 2H), 3.23-3.14 (m, 4H), 2.49-2.44 (m, 4H), 2.24 (s, 3H). 13C-NMR (101 MHz, DMSO) δ=152.27 (Cq), 149.85 (Cq), 145.83 (CH), 137.99 (Cq), 132.28 (Cq), 131.46 (2 CH), 131.23 (Cq), 129.68 (CH), 128.97 (2 CH), 126.94 (2 CH), 125.66 (CH), 122.62 (Cq), 121.43 (Cq), 120.52 (Cq), 118.69 (CH), 116.77 (CH), 115.58 (2 CH), 114.46 (Cq), 111.68 (CH), 96.75 (Cq), 86.54 (Cq), 54.42 (2 CH2), 47.87 (2 CH2), 45.54 (CH3). HRMS (ESI): calcd. for C30H27N4: 443.2230. found: 443.2247.

Sources & evidence

ORD record
ord-cf3a36056b5e41118bfdf1c9abd8ae18
Source dataset
uspto-grants-2016_08
Patent number
US09428500B2

Reaction notes

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