HCID 72191830, compound → HCID 178424960, compound

HRID 2174027Notes

Reaction equation

HRID 2174027 reaction equation
[NH2:1][CH:2]([C:14]1[C:22]([CH2:23][CH3:24])=[CH:21][C:20]([CH3:25])=[C:19]2[C:15]=1[CH:16]=[CH:17][NH:18]2)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=2[N:4]=1.[CH:26](C1C=C(C)C2N(S(C3C=CC(C)=CC=3)(=O)=O)C=CC=2C=1C=O)(C)C>>[NH2:1][CH:2]([C:14]1[C:22]([CH:23]([CH3:26])[CH3:24])=[CH:21][C:20]([CH3:25])=[C:19]2[C:15]=1[CH:16]=[CH:17][NH:18]2)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 72191830HCID 72191830, compoundHCID 178435866HCID 178435866, compound

Product 1

HCID 178424960HCID 178424960, compound

Procedure

The title compound was synthesized following the same procedures that led to 2-(amino(5-ethyl-7-methyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 96) starting from 5-Isopropyl-7-methyl-1-tosyl-1H-indole-4-carbaldehyde (Example 50-A). 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 9.50 (br. s., 1H), 8.00 (s, 1H), 7.60 (d, J=8.30 Hz, 1H), 7.56 (dd, J=1.50, 8.30 Hz, 1H), 7.05-7.20 (m, 2H), 6.55 (s, 1H), 5.71-5.88 (m, 1H), 3.33-3.48 (m, 1H), 2.52 (s, 3H), 1.36 (d, J=6.82 Hz, 3H), 1.21-1.33 (m, 3H). HRMS calcd. for C21H21N5 (M+H)+ 344.1870. found 344.1865.

Sources & evidence

ORD record
ord-8fd137c4187541a9ae0ef615ffb6f12c
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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