N-Methyloxindole → HCID 178481479, compound

HRID 1615241Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[NH:12]1[C:16]2[CH:17]=[C:18]([CH:21]=O)[CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1>>[NH:14]1[C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[C:4]3/[C:3](=[O:11])[N:2]([CH3:1])[C:10]4[C:5]/3=[CH:6][CH:7]=[CH:8][CH:9]=4)=[CH:17][C:16]=2[N:12]=[N:13]1

Participants

Reactant 2

HCID 6096N-Methyloxindole

HCID 178519388HCID 178519388, compound

Product 1

HCID 178481479HCID 178481479, compound

Procedure

The title compound was synthesized according to the method described for Example A11B, except substituting 1-methylindolin-2-one (18 mg, 0.124 mmol) and 1H-benzo[d][1,2,3]triazole-6-carbaldehyde (20 mg, 0.136 mmol) and then purified by preparatory HPLC to obtain 3.4 mg, 10% of a yellow solid. 1H NMR (400 MHz, CD3OD) δ 8.23 (bs, 1H), 8.00 (bs, 1H), 7.95 (s, 1H), 7.84-7.75 (m, 1H), 7.59 (d, J=7.58 Hz, 1H), 7.34 (t, J=8.00 Hz, 1H), 7.04 (d, J=7.83 Hz, 1H), 6.92 (d, J=7.58 Hz, 1H), 3.35 (s, 3H); MS ESI 277.0 [M+H]+, calcd for [C16H12N4O+H]+ 277.11.

Workup

custompurified by preparatory HPLC

Sources & evidence

ORD record: ord-d536710c7c214728928df2a6e2d8e74f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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