Dimethylamine → HCID 18387443, compound

HRID 2296745Notes

Reaction equation

CS([CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]=2[S:8]1)(=O)=O.[CH3:29][NH:30][CH3:31]>O1CCCC1>[CH3:29][N:30]([CH3:31])[CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]=2[S:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(2-methanesulfonylethyl)-5-(4-nitrobenzoyl)-1,5-benzothiazepine as prepared in Example 6 (0.9 g, 2.1 mM) and dimethylamine (40% solution in water, 3.0 ml) in tetrahydrofuran (10 ml) was heated in a sealed tube with stirring in an 80° C. oil bath for 16 hours. The mixture was cooled to room temperature, evaporated to dryness, diluted with water (30 ml) and extracted with ethyl acetate (2×35 ml). The combined ethyl acetate extracts were dried (MgSO4) and evaporated in vacuo to give the desired product (0.78 g, 97%). This product (0.78 g, 2.0 mM) was dissolved in ethanol, and a catalytic amount of 10% Pd/C was added. The mixture was hydrogenated in a PARR apparatus under 30 psi of H2 pressure for 16 hr, filtered through Celite and evaporated in vacuo to give the desired product (0.64 g, 90%). m/z (M+) 356.

Workup

temperaturewas heated in a sealed tube
temperatureThe mixture was cooled to room temperature
customevaporated to dryness
additiondiluted with water (30 ml)
extractionextracted with ethyl acetate (2×35 ml)
dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-f6eb58ea398544c3a68d0a8194faf450
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489321B1

Reaction notes

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