HCID 86701575, compound → HCID 178467649, compound

HRID 2174001Notes

Reaction equation

HRID 2174001 reaction equation
[CH3:1][C:2]1[C:3]([CH:22]([O:42][CH2:43][CH3:44])[C:23]2[N:27](COCC[Si](C)(C)C)[C:26]3[CH:36]=[CH:37][C:38]([C:40]#[N:41])=[CH:39][C:25]=3[N:24]=2)=[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(OCC)C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=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]([O:42][CH2:43][CH3:44])[C:23]2[NH:27][C:26]3[CH:36]=[CH:37][C:38]([C:40]#[N:41])=[CH:39][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 86701575HCID 86701575, compoundHCID 86701576HCID 86701576, compound

Product 1

HCID 178467649HCID 178467649, compound

Procedure

The title compound was synthesized from a mixture of (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(ethoxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)(ethoxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile as described in Example 64-B and 64-C. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 10.96 (br.s, 1H) 7.98 (s, 1H) 7.65 (d, J=8.25 Hz, 1H) 7.55 (m, 1H) 7.21 (t, J=2.78 Hz, 1H) 6.74 (s, 1H) 6.56 (dd, J=2.78, 2.02 Hz, 1H) 6.30 (s, 1H) 3.56-3.64 (m, 1H) 3.42-3.50 (m, 1H) 2.42 (s, 3H) 2.41 (s, 3H) 1.22 (t, J=6.95 Hz, 3H). HRMS calcd. for C21H20N4O (M+H)+ 345.1710. found 345.1717.

Sources & evidence

ORD record
ord-d94d73b32add460fb34202fcbc3dce2e
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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