HCID 86701521, compound → HCID 178489068, compound

HRID 2173958Notes

Reaction equation

HRID 2173958 reaction equation
[C:1]([C:3]1[CH:46]=[CH:45][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([CH:10]([NH:30]S(C(C)(C)C)=O)[C:11]3[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[C:16]4[C:12]=3[CH:13]=[CH:14][N:15]4C(OC(C)(C)C)=O)=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(NS(C(C)(C)C)=O)C3C(OC)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)N(COCC[Si](C)(C)C)C=2C=1)#N>>[NH2:30][CH:10]([C:11]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)[C:8]1[NH:7][C:6]2[CH:45]=[CH:46][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1

Participants

3

Reactant 2

HCID 86701521HCID 86701521, compoundHCID 86701522HCID 86701522, compound

Product 1

HCID 178489068HCID 178489068, compound

Procedure

The title compound was synthesized from a mixture of (±)-tert-butyl 4-((5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(1,1-dimethylethylsulfinamido)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(1,1-dimethylethylsulfinamido)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate following the same procedure as described in Example 36-E. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.91 (br. s., 1H) 7.91 (s, 1H) 7.57 (d, J=8.08 Hz, 1H) 7.47 (dd, J=8.34, 1.52 Hz, 1H) 7.19 (t, J=2.78 Hz, 1H) 6.74 (s, 1H) 6.23 (dd, J=3.03, 2.02 Hz, 1H) 5.80 (s, 1H) 3.71 (s, 3H) 2.44 (s, 3H). HRMS calcd. for C19H17N5O (M+H)+ 332.1506. found 332.1507.

Sources & evidence

ORD record
ord-6a5770eb8ff940ed8cb0e632216d8308
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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