HCID 86701459, compound → HCID 178429690, compound

HRID 2173918Notes

Reaction equation

[OH:1][C:2]([C:26]1[N:30](COCC[Si](C)(C)C)[C:29]2[CH:39]=[C:40]([C:43]#[N:44])[CH:41]=[CH:42][C:28]=2[N:27]=1)([C:4]1[C:12](SC)=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2S(C1C=CC(C)=CC=1)(=O)=O)[CH3:3].OC(C1N(COCC[Si](C)(C)C)C2C=CC(C#N)=CC=2N=1)(C1C(SC)=CC(C)=C2C=1C=CN2[S:60]([C:63]1C=CC(C)=CC=1)(=[O:62])=[O:61])C>>[OH:1][C:2]([C:26]1[NH:27][C:28]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][C:29]=2[N:30]=1)([C:4]1[C:12]([S:60]([CH3:63])(=[O:62])=[O:61])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH3:3]

Participants

Reactant 2

HCID 86701459HCID 86701459, compound

HCID 86701460HCID 86701460, compound

Product 1

HCID 178429690HCID 178429690, compound

Procedure

A mixture of (±)-2-(1-hydroxy-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile and (±)-2-(1-hydroxy-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile was transformed into the title compound using the same reaction conditions as described in Example 10-B and Example 10-C. 1H NMR (400 MHz, DMSO-d6) δ 12.24-12.49 (m, 1H), 11.46 (br. s., 1H), 8.17-8.32 (m), 7.70-7.84 (m, 2H), 7.54 (m, 1H), 7.45 (m), 7.18 (t, J=2.91 Hz, 1H), 6.49-6.69 (m, 1H), 5.63 (dt, J=1.83, 3.82 Hz, 1H), 3.55 (s, 3H), 2.51 (s, 3H), 2.27 (s, 3H). HRMS calcd. for C20H18N4O3S (M+H)+ 395.1173. found 395.1173.

Sources & evidence

ORD record: ord-80c8e84e0df645d68af9200ba9fe7f06
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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