Triethyl orthoacetate → 4-[4-(Cyclopropylmethoxy)-2-methyl-1H-benzimidazol-5-yl]-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056950Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)=[C:4]([C:9]2[C:10]3[CH:19]=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]=3[C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[C:35](OCC)(OCC)(OCC)[CH3:36]>>[CH:32]1([CH2:31][O:30][C:3]2[C:2]3[N:1]=[C:35]([CH3:36])[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:9]2[C:10]3[CH:19]=[CH:18][NH:17][C:11]=3[C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)[CH2:33][CH2:34]1

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 1180939054-[3,4-Diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Product 1

HCID 1180939714-[4-(Cyclopropylmethoxy)-2-methyl-1H-benzimidazol-5-yl]-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Procedure

This compound was synthesized according to the procedure of Example 2 using 4-[3,4-diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one as the starting material and triethyl orthoacetate instead of ethyl orthoformate. 1H NMR (300 MHz, DMSO-d6) δ 12.23 (s, 1H), 11.99 (s, 0.3H), 11.93 (s, 0.7H), 7.33-7.19 (m, 1.2H), 7.18-7.00 (m, 2.8H), 6.17-6.10 (m, 0.3H), 6.10-6.02 (m, 0.7H), 4.37 (d, J=6.8 Hz, 2H), 3.62-3.51 (m, 3H), 1.09-0.89 (m, 1H), 0.41-0.25 (m, 2H), 0.17-0.06 (m, 1.4H), −0.01-−0.12 (m, 0.6H); LCMS calculated for C20H21N4O2 (M+H)+: m/z=349.2. found: 349.1.

Workup

customThis compound was synthesized

Sources & evidence

ORD record: ord-b706f92f1b484a85937f116da2a0cf79
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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