Chlorosuccinimide → HCID 178424043, compound

HRID 2174015Notes

Reaction equation

HRID 2174015 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1C(=O)N([Cl:31])C(=O)C1>>[Cl:31][C:5]1[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[C:3]=2[CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)[NH:7][CH:6]=1

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 178424030HCID 178424030, compound

Product 1

HCID 178424043HCID 178424043, compound

Procedure

The title compound was synthesized by a chlorination of 2-((5,7-dimethyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile using NCS analogously to the preparation of Example 85. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.38 (s, 1H) 11.29 (br. s., 1H) 7.98 (d, J=0.76 Hz, 1H) 7.75-7.87 (m, 1H) 7.61 (d, J=8.34 Hz, 1H) 7.44-7.55 (m) 7.39-7.44 (m) 6.86 (s, 1H) 4.75 (d, J=4.55 Hz, 2H) 2.42 (s, 3H) 2.24 (s, 3H). HRMS calcd. for C13H16ClN4 (M+H)+ 335.1058. found 335.1062.

Workup

  1. customanalogously to the preparation of Example 85

Sources & evidence

ORD record
ord-22086d162b3f49929b89fd5d43672d1b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…