Trans-4-amino-1-methyl-cyclohexanol → HCID 67500443, compound

HRID 1631330Notes

Reaction equation

HRID 1631330 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5]([CH3:9])([OH:8])[CH2:4][CH2:3]1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]1[CH:28]=[CH:27][N:26]2[N:29]=[CH:30][C:31]([C:32](O)=[O:33])=[C:25]2[N:24]=1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]1[CH:28]=[CH:27][N:26]2[N:29]=[CH:30][C:31]([C:32]([NH:1][CH:2]3[CH2:7][CH2:6][C:5]([OH:8])([CH3:9])[CH2:4][CH2:3]3)=[O:33])=[C:25]2[N:24]=1

Participants

3

Reactant 2

HCID 18331273Trans-4-amino-1-methyl-cyclohexanolHCID 66847716HCID 66847716, compound

Product 1

HCID 67500443HCID 67500443, compoundYield 48%

Procedure

The minor isomer from Step A (45.1 mg, 0.197 mmol) was dissolved in DCM (1.0 mL) and 4N HCl in dioxane (492 μL, 1.97 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour and was concentrated to afford 4-amino-1-methylcyclohexanol (minor isomer). The 4-amino-1-methylcyclohexanol was reacted with (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation C) according to the procedure outlined in Example 1 to provide the title product as a white solid (14 mg, 48% yield). MS (apci) m/z=456.1 (M+H).

Sources & evidence

ORD record
ord-8a6f7c30e5e1445abb30acd28114293f
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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