Sodium Hydroxide → HCID 21072794, compound

HRID 1372893Notes

Reaction equation

COCCO[AlH2-]OCCOC.[Na+].CO[C:15](=O)[NH:16][C:17]1[CH:18]=[N:19][C:20]([N:31]2[CH2:36][CH2:35][S:34][CH2:33][CH2:32]2)=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:15][NH:16][C:17]1[CH:18]=[N:19][C:20]([N:31]2[CH2:32][CH2:33][S:34][CH2:35][CH2:36]2)=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

43.7 ml Red-Al (3.5 M in toluene) was diluted in 25 ml toluene and added dropwise to a solution of 13 g (30.6 mmol) [4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-carbamic acid methyl ester in 55 ml toluene at 10° C. (the addition was exothermic). The yellow solution obtained was stirred for 40 minutes at room temperature and 1.5 hours at 50° C. It was cooled to 0° C. and poured slowly onto a mixture of 150 ml 4 N aqueous sodium hydroxide and 50 ml ice (very exothermic). After 10 minutes stirring, the phases were separated, the aqueous phase was extracted with tert-butyl-methyl-ether and the organic phases were washed with brine. The combined organic extracts were dried and concentrated under reduced pressure to yield 10 g methyl-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-amine as a brown oil which was used in the next step without further purification.

Workup

additionthe addition
customThe yellow solution obtained
temperatureIt was cooled to 0° C.
stirringAfter 10 minutes stirring
customthe phases were separated
extractionthe aqueous phase was extracted with tert-butyl-methyl-ether
washthe organic phases were washed with brine
customThe combined organic extracts were dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0f1e6ebcf02047a28d92e4c758403db7
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160881B2

Reaction notes

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