Ethyl Acetate → HCID 89832319, compound

HRID 338144Notes

Reaction equation

CN(C)C(N(C)C)=N.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]12[CH2:24][NH:23][CH2:22][CH:21]1[CH2:20][S:19][C:18]([NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:17]2.[F:34][C:35]1[CH:36]=[N:37][C:38](Cl)=[N:39][CH:40]=1.C(OCC)(=O)C>CS(C)=O.O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]12[CH2:24][N:23]([C:38]3[N:39]=[CH:40][C:35]([F:34])=[CH:36][N:37]=3)[CH2:22][CH:21]1[CH2:20][S:19][C:18]([NH:25][C:26](=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[N:17]2

Participants

Conditions

Temperature: 100 °C

Procedure

N,N,N′,N′-tetramethylguanidine (0.44 mL, 3.5 mmol) is added to a solution of racemic N-[7a-(2-fluorophenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (1.0 g, 2.9 mmol) and 5-fluoro-2-chloropyrimidine (0.46 g, 3.5 mmol) in dimethylsulfoxide (10 mL). The reaction is stirred at 100° C. for 2 hours, and cooled to room temperature. To the crude reaction is added ethyl acetate (7.5 ml) and water (2.5 ml), the mixture is passed through diatomaceous earth (10 g), and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with a gradient of 40% to 60% ethyl acetate in hexanes to give the title compound (560 mg, 43%). ES/MS (m/e): 452 (M+H).

Workup

temperaturecooled to room temperature
customTo the crude reaction
customthe solvent removed under reduced pressure
customThe residue is purified by silica gel chromatography
washeluting with a gradient of 40% to 60% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-4117dc7abf184c8681fcb5aba07beaf3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889856B2

Reaction notes

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