1H-Indazol-5-amine → HCID 136391300, compound

HRID 1615295Notes

Reaction equation

HRID 1615295 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:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[CH:17]2>O>[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]([F:1])[CH:3]=4)[NH:7][C:6]3=[O:11])=[CH:22][CH:21]=2)[CH:17]=[N:18]1

Participants

4

Reactant 2

HCID 880121H-Indazol-5-amineHCID 2365665-Fluoroisatin

Product 1

HCID 136391300HCID 136391300, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (62 mg, 43%) was synthesized as a brick red solid (instead of stirring at it, 1 mL of H2O was added to crash out the product) according to the method described for Example A74 using 5-fluoroisatin (82.5 mg, 0.5 mmol), 5-aminoindazole (66.5 mg, 0.5 mmol). 1H NMR indicated a 3:1 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.22 (s, 1H), 11.00 (s, 1H), 8.10 (s, 1H), 6.67 (d, J=8.8 Hz, 1H), 7.39 (s, 1H), 7.22 (dt, J=9.2 Hz, 2.4 Hz, 1H), 7.10 (dd, J=8.8 Hz, 1.6 Hz, 1H), 6.90 (dd, J=8.8 Hz, 4.4 Hz, 1H), 6.14 (dd, J=8.8 Hz, 2.8 Hz, 1H); MS ESI 281.0 [M+H]+, calcd for [C15H9FN4O+H]+ 281.1.

Workup

  1. additionwas added
  2. additiona 3:1 mixture of E/Z isomers

Sources & evidence

ORD record
ord-ade9b9bc7ff348daa0920012cb85aa98
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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