1H-Indazol-6-amine → HCID 135912038, compound

HRID 1615291Notes

Reaction equation

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

Participants

Reactant 2

HCID 814231H-Indazol-6-amine

HCID 2365665-Fluoroisatin

Product 1

HCID 135912038HCID 135912038, compoundYield 54.2%

Procedure

The title compound (76 mg, 54%) was synthesized as a dark red solid according to the method described for Example A74 using 5-fluoroisatin (82.5 mg, 0.5 mmol) and 6-aminoindazole (66.5 mg, 0.5 mmol). NMR analysis indicated a 79:21 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.08 (s, 1H, NH), 11.03 (s, 1H, NH), 8.11 (s, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.22 (dt, J=9.2 Hz, 2.8 Hz, 1H), 6.90 (dd, J=8.4 Hz, 4.4 Hz, 1H), 6.82-6.77 (m, 1H), 5.98 (dd, J=8.0 Hz, 2.0 Hz, 1H); MS ESI 281.0 [M+H]+, calcd for [C15H9FN4O+H]+ 281.1.

Workup

additiona 79:21 mixture of E/Z isomers

Sources & evidence

ORD record: ord-e328c43a06d2426daa1226d6c8134dc3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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