5-Methylisatin → HCID 136331583, compound

HRID 1615294Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[CH:17]2>>[NH:19]1[C:20]2[C:16](=[CH:15][C:14]([N:13]=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=4)[NH:7][C:6]3=[O:11])=[CH:22][CH:21]=2)[CH:17]=[N:18]1

Participants

Reactant 2

HCID 118405-Methylisatin

HCID 880121H-Indazol-5-amine

Product 1

HCID 136331583HCID 136331583, compoundYield 60.1%

Procedure

The title compound (83 mg, 60%) was synthesized as a brown solid according to the method described for Example A74 using 5-methylisatin (80.5 mg, 0.5 mmol), 5-aminoindazole (66.5 mg, 0.5 mmol). 1H NMR indicated a 78:22 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.15 (s, 1H, NH), 10.86 (s, 1H, NH), 8.08 (s, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.07 (dd, J=8.8 Hz, 1H), 6.79 (d, J=8.0 Hz, 1H) 6.33 (s, 1H), 1.89 (s, 3H); MS ESI 277.0 [M+H]+, calcd for [C16H12N4O+H]+ 277.1.

Workup

additiona 78:22 mixture of E/Z isomers

Sources & evidence

ORD record: ord-5017e0f3eb4841d4bf918916e88274d5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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