HCID 86701497, compound → HCID 178429087, compound

HRID 2173941Notes

Reaction equation

[NH2:1][C:2](=[O:44])[CH2:3][O:4][C:5]1[C:6]([C:22]([C:25]2[N:29](COCC[Si](C)(C)C)[C:28]3[CH:38]=[CH:39][C:40]([C:42]#[N:43])=[CH:41][C:27]=3[N:26]=2)([OH:24])[CH3:23])=[C:7]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[N:10](C(OC(C)(C)C)=O)[CH:9]=[CH:8]2.NC(=O)COC1C(C(C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)(O)C)=C2C(=C(C)C=1)N(C(OC(C)(C)C)=O)C=C2>>[C:42]([C:40]1[CH:39]=[CH:38][C:28]2[NH:29][C:25]([C:22]([C:6]3[C:5]([O:4][CH2:3][C:2]([NH2:1])=[O:44])=[CH:13][C:12]([CH3:14])=[C:11]4[C:7]=3[CH:8]=[CH:9][NH:10]4)([OH:24])[CH3:23])=[N:26][C:27]=2[CH:41]=1)#[N:43]

Participants

Reactant 2

HCID 86701497HCID 86701497, compound

HCID 86701498HCID 86701498, compound

Product 1

HCID 178429087HCID 178429087, compound

Procedure

The title compound was synthesized from a mixture of (±)-tert-butyl 5-(2-amino-2-oxoethoxy)-4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxyethyl)-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 5-(2-amino-2-oxoethoxy)-4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxyethyl)-7-methyl-1H-indole-1-carboxylate as described in Example 24-B. 1H NMR (TFA salt, 400 MHz, MeOH-d4) δ ppm 8.04 (s, 1H) 7.63-7.85 (m, 2H) 7.31 (d, J=3.28 Hz, 1H) 7.01 (d, J=3.28 Hz, 1H) 6.69 (s, 1H) 4.37-4.49 (m, 1H) 4.24-4.35 (m, 1H) 2.49 (s, 3H) 2.31 (s, 3H). HRMS calcd. for C21H19N5O3 (M+H)+ 390.1561. found 390.1561.

Sources & evidence

ORD record: ord-6467dfd7c9274157983d1825ceca6c53
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

Loading…