1-(2-methanesulfonyl-pyrimidin-4-yl)-3-methoxy-1H-indazole → HCID 178494301, compound

HRID 1947005Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.CS([C:13]1[N:18]=[C:17]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([O:28][CH3:29])=[N:20]2)[CH:16]=[CH:15][N:14]=1)(=O)=O>CN1C(=O)CCC1>[CH3:29][O:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:1][C@H:2]3[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]3)[N:18]=2)[N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

trans-4-Aminocyclohexanol (870 mg, 8 mmol) was added to 1-(2-methanesulfonyl-pyrimidin-4-yl)-3-methoxy-1H-indazole (440 mg, 1 mmol) in NMP (15 mL), and the resulting mixture heated to 120° C. for 3 h. The reaction mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude yellow solid. This crude material was purified by flash chromatography (MeOH/DCM, 5:95) and recrystallized from DCM/hexanes to give trans-4-[4-(3-methoxy-indazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (181 mg (37% yield) as a white solid. MS=340 [M+H]+; MP=202.3-205.1° C.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between EtOAc and water
customThe organic layer was separated
washwashed with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a crude yellow solid
customThis crude material was purified by flash chromatography (MeOH/DCM, 5:95)
customrecrystallized from DCM/hexanes

Sources & evidence

ORD record: ord-03db48b7ca78442fb0137817419b05ac
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399462B2

Reaction notes

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