Isatin → HCID 136331586, compound

HRID 1615293Notes

Reaction equation

HRID 1615293 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[CH:16]2>CC(O)=O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([N:12]=[C:4]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:1][C:2]3=[O:3])=[CH:21][CH:20]=2)[CH:16]=[N:17]1

Participants

4

Reactant 2

HCID 7054IsatinHCID 880121H-Indazol-5-amine

Product 1

HCID 136331586HCID 136331586, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

The title compound (165 mg, 63%) was synthesized as a yellow solid according to the method described for Example A74 using isatin (147 mg, 1 mmol), 5-aminoindazole (133 mg, 1 mmol) and 2 drops of HOAc. 1H NMR indicated a 5:1 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.17 (s, 1H, NH), 11.00 (s, 1H, NH), 8.07 (s, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.35 (s, 1H), 7.31 (t, J=7.6 Hz, 1H), 7.07 (dd, J=9.2 Hz, 1.6 Hz, 1H), 6.88 (d, J=8.0 Hz, 1H), 6.67 (t, J=8.0 Hz, 1H), 6.45 (d, J=7.6 Hz, 1H); MS ESI 263.0 [M+H]+, calcd for [C15H10N4O+H]+ 263.1.

Workup

  1. additiona 5:1 mixture of E/Z isomers

Sources & evidence

ORD record
ord-8987947b1d0546a5b76b604d1722b721
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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