1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517367, compound

HRID 1615288Notes

Reaction equation

HRID 1615288 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][C:24]([CH:28]=O)=[CH:25][CH:26]=2)[NH:21][N:20]=1>>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][C:24](/[CH:28]=[C:3]3/[C:2](=[O:10])[NH:1][C:5]4[C:4]/3=[CH:9][CH:8]=[CH:7][N:6]=4)=[CH:25][CH:26]=2)[NH:21][N:20]=1

Participants

3

Reactant 2

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 86651961HCID 86651961, compound

Product 1

HCID 178517367HCID 178517367, compoundYield 28.2%

Procedure

The title compound (7 mg, 21%) was synthesized as yellow solid according to the method described for Example A67 using 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (9.3 mg, 0.07 mmol) and (E)-3-(2-(pyridin-2-yl)vinyl)-1H-indazole-6-carbaldehyde (17 mg, 0.068 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.53 (s, 1H, NH), 11.27 (s, 1H, NH), 8.62 (d, J=4.0 Hz, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.12 (d, J=5.2 Hz, 1H), 8.02-7.89 (m, 4H), 7.82 (t, J=8.0 Hz, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.63 (d, J=16.8 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.28 (t, J=6.0 Hz, 1H), 6.91 (dd, J=7.6 Hz, 5.6 Hz, 1H); MS ESI 366.1 [M+H]+, calcd for [C22H15N5O+H]+ 366.1.

Sources & evidence

ORD record
ord-5630e292273c47a0bf7c246e18608d71
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…