HCID 86701577, compound → HCID 178424032, compound

HRID 2174002Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH:22]([C:24]2[N:28](COCC[Si](C)(C)C)[C:27]3[CH:37]=[CH:38][C:39]([C:41]#[N:42])=[CH:40][C:26]=3[N:25]=2)[CH3:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[CH:5]2.CC1C(C(C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)C)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2>>[CH3:1][C:2]1[C:3]([CH:22]([C:24]2[NH:28][C:27]3[CH:37]=[CH:38][C:39]([C:41]#[N:42])=[CH:40][C:26]=3[N:25]=2)[CH3:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

Reactant 2

HCID 86701577HCID 86701577, compound

HCID 86701578HCID 86701578, compound

Product 1

HCID 178424032HCID 178424032, compound

Procedure

The title compound was synthesized from a mixture of (±)-2-(1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile as described in Example 64-B and 64-C. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.22 (br. s., 1H) 10.86 (br. s., 1H) 8.13 (m) 7.69-7.84 (m) 7.36-7.54 (m) 7.05 (t, J=2.78 Hz, 1H) 6.76 (s, 1H) 5.83-5.96 (m, 1H) 4.72-4.90 (m, 1H) 2.39 (s, 3H) 2.37 (s, 3H) 1.76 (d, J=7.07 Hz, 3H). HRMS calcd. for C20H18N4 (M+H)+ 315.1610. found 315.1610.

Sources & evidence

ORD record: ord-a82a121dc56a459fb5ac512af0bb60b1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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