Ethyl Acetate → HCID 89832319, compound

HRID 470265Notes

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-7fa93452abe24164a03d87bc9b6588cf
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629270B2

Reaction notes

Loading…