HCID 86701586, compound → HCID 178435867, compound

HRID 2174005Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([CH:23]([OH:43])[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)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8](S(C1C=CC(C)=CC=1)(=O)=O)[CH:7]=[CH:6]2)[CH3:2].C(C1C(C(O)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)C>>[CH2:1]([C:3]1[CH:11]=[C:10]([CH3:12])[C:9]2[NH:8][CH:7]=[CH:6][C:5]=2[C:4]=1[C:23]([C:24]1[NH:28][C:27]2[CH:37]=[CH:38][C:39]([C:41]#[N:42])=[CH:40][C:26]=2[N:25]=1)=[O:43])[CH3:2]

Participants

Reactant 2

HCID 86701586HCID 86701586, compound

HCID 86701587HCID 86701587, compound

Product 1

HCID 178435867HCID 178435867, compound

Procedure

The title compounds was synthesized as in Example 25A and 25-B from (±)-2-((5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (Example 70-A). 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 9.42 (br. s., 1H), 8.12 (dd, J=0.76, 1.39 Hz, 1H), 7.79 (dd, J=0.76, 8.59 Hz, 1H), 7.62 (dd, J=1.50, 8.60 Hz, 1H), 7.22 (dd, J=2.90, 3.03 Hz, 1H), 6.99 (s, 1H), 6.06 (dd, J=2.02, 3.03 Hz, 1H), 2.63 (q, J=7.58 Hz, 2H), 2.55 (d, J=0.88 Hz, 3H), 1.14 (t, J=7.58 Hz, 3H). HRMS calcd. for C20H16N4O (M+H)+ 329.1397. found 329.1327.

Sources & evidence

ORD record: ord-fe0eeb818b774323bc9dbfd0b4475283
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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