HCID 86701499, compound → HCID 178429105, compound

HRID 2173942Notes

Reaction equation

[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([C:13]3[C:21]([O:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:20][C:19]([CH3:28])=[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(OCC(OC)=O)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)(O)C)N(COCC[Si](C)(C)C)C=2C=1)#N>>[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[NH:7][C:8]([C:10]([C:13]3[C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:20][C:19]([CH3:28])=[C:18]4[C:14]=3[CH:15]=[CH:16][NH:17]4)([OH:12])[CH3:11])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 86701499HCID 86701499, compound

HCID 86701500HCID 86701500, compound

Product 1

HCID 178429105HCID 178429105, compound

Procedure

A mixture of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxyethyl)-5-(2-methoxy-2-oxoethoxy)-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-(2-methoxy-2-oxoethoxy)-7-methyl-1H-indole-1-carboxylate was fully deprotected using the same procedure as described in Example 24-B to give the title compound. 1H NMR (TFA salt, 400 MHz, MeOH-d4) δ ppm 8.06 (s, 1H) 7.79 (s, 2H) 7.31 (d, J=3.28 Hz, 1H) 6.92 (d, J=3.28 Hz, 1H) 6.70 (s, 1H) 4.49 (m, 2H) 2.50 (s, 3H) 2.30 (s, 3H). HRMS calcd. for C21H18N4O4 (M+H)+ 391.1401. found 391.1394.

Sources & evidence

ORD record: ord-a30dcd1497fe4b108a8484f81c692745
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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