3-Aminobenzyl alcohol → HCID 86591964, compound

HRID 1714432Notes

Reaction equation

HRID 1714432 reaction equation
[N:1]1([C:6]([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([O:17][CH3:18])[CH:14]=3)[C:9]2=[O:21])=[S:7])[CH:5]=[CH:4]N=C1.N[C:23]1[CH:24]=[C:25]([CH:28]=CC=1)[CH2:26][OH:27]>C1COCC1>[OH:27][CH2:26][C:25]1[CH:28]=[C:5]([NH:1][C:6]([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([O:17][CH3:18])[CH:14]=3)[C:9]2=[O:21])=[S:7])[CH:4]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 802933-Aminobenzyl alcoholHCID 18445515HCID 18445515, compound

Product 1

HCID 86591964HCID 86591964, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Imidazole-1-carbothioyl)-5,6-dimethoxy-indan-1-one, Intermediate B, (1.0 g, 3.3 mmol) was mixed with 3-aminobenzyl alcohol (0.40 g, 3.3 mmol), and 30 mL THF in a flask. 5,6-Dimethoxy-1-oxo-indan-2-carbothioic acid (3-hydroxymethyl-phenyl)-amide was obtained after stirring the reaction mixture for 4 hours at room temperature. HPLC/MS m/z 358 (M+H)+. The intermediate was not isolated, the mixture was mixed with hydrazine (0.13 mL, 4 mmol), and acetic acid (2-3 drops). The reaction was heated at 78° C. for 12 hours. The reaction solution was then diluted with ethyl acetate, washed with water, and dried over Na2SO4. The solvent was removed and the title compound was purified by HPLC with a C-18 reversed phase column and CH3CN—H2O-TFA as gradient solvents. The title compound, [3-(6,7-Dimethoxy-2,4-dihydro-indeno[1,2-c]pyrazol-3-ylamino)-phenyl]-methanol, Compound 36, was obtained as a solid TFA salt. MS m/z 338 (M+H)+; HPLC:100% (uv 214 mu); 1HNMR (DMSO-d6): 3.40(s, 2H), 4.54(s, 2H), 6.81 (d, 1H), 7.02 (d, 1H), 7.14(s, 1H), 7.22(d, 2H).

Sources & evidence

ORD record
ord-ba8495e8e31a43b385a3eb4d45f78ca7
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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