HCID 86701488, compound → HCID 178489066, compound

HRID 2173936Notes

Reaction equation

[C:1]([C:3]1[CH:41]=[CH:40][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([C:13]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4C(OC(C)(C)C)=O)([OH:12])[CH3:11])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(OC)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)(O)C)N(COCC[Si](C)(C)C)C=2C=1)#N>>[OH:12][C:10]([C:8]1[NH:7][C:6]2[CH:40]=[CH:41][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)[CH3:11]

Participants

Reactant 2

HCID 86701488HCID 86701488, compound

HCID 86701489HCID 86701489, compound

Product 1

HCID 178489066HCID 178489066, compound

Procedure

(±)-tert-Butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate was converted in the title compound using the same procedure described in Example 24-B. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.30 (s, 1H) 10.86 (br. s., 1H) 8.10 (s) 7.63-7.84 (m) 7.38-7.55 (m, 2H) 7.21 (q, J=3.12 Hz, 1H) 6.47-6.77 (m, 1H) 6.00 (d, J=1.01 Hz, 1H) 3.26-3.30 (m, 3H) 2.40-2.45 (m, 3H) 2.03 (s, 3H). HRMS calcd. for C20H18N4O2 (M+H)+ 347.1508. found 347.1510.

Sources & evidence

ORD record: ord-69f7fe952db7497ea8d535edc1cf96c4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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