Monomethylamine methanol → HCID 69429749, compound

HRID 1269995Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]1[C:11]([O:12][C@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2.CN.CO>>[F:30][C:2]([F:1])([F:31])[C:3]1[C:11]([O:12][C@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH2:19])[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2

Participants

Reactant 2

HCID 57454252Monomethylamine methanol

HCID 69431517HCID 69431517, compound

Product 1

HCID 69429749HCID 69429749, compoundYield 31.2%

Procedure

A mixture of the crude product 2-{trans-3-[(4-trifluoromethyl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (0.324 g) and a 30% methylamine/methanol solution (15 ml) was stirred at 90° C. for 3 hours. The solvent was distilled off and the residue solid was purified by elution by a silica gel column chromatography (chloroform/methanol=20:1→chloroform/methanol/triethylamine=10:1:1) to obtain trans-3-[(4-trifluoromethyl-1H-indazol-5-yl)oxy]cyclohexylamine (70.4 mg, 16%, two steps).

Workup

distillationThe solvent was distilled off
customthe residue solid was purified by elution by a silica gel column chromatography (chloroform/methanol=20:1→chloroform/methanol/triethylamine=10:1:1)

Sources & evidence

ORD record: ord-01635be234b1450d963fd80e1aec860b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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