Ammonium Hydroxide → HCID 86670374, compound

HRID 1972512Notes

Reaction equation

Cl[C:2]1[S:3][C:4]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=3)[C@@H:12]([CH3:32])[CH2:11]2)(=[O:9])=[O:8])=[CH:5][N:6]=1.[NH4+:33].[OH-]>CCO.CCOC(C)=O>[NH2:33][C:2]1[S:3][C:4]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=3)[C@@H:12]([CH3:32])[CH2:11]2)(=[O:9])=[O:8])=[CH:5][N:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-(2-((2S)-4-((2-chloro-1,3-thiazol-5-yl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1,3,3,3-hexafluoro-2-propanol (185 mg, 0.352 mmol) in 2 mL of EtOH and 2 mL of 30% NH4OH was heated to 140° C. for 30 min. Afterwards, the solution was diluted with EtOAc (20 mL). The solution was transferred to a reparatory funnel and washed with water (10 mL) and brine (10 mL). The combined organics were dried over MgSO4, filtered, and concentrated. The crude material was absorbed onto silica gel and purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2) to give 2-(2-((2S)-4-((2-amino-1,3-thiazol-5-yl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1,3,3,3-hexafluoro-2-propanol (132 mg).

Workup

customThe solution was transferred to a reparatory funnel
washwashed with water (10 mL) and brine (10 mL)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was absorbed onto silica gel
custompurified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-2e4fc0d2d87d4e6e8dcfd97b57e4e47d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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