Ethyl Acetate → HCID 89832319, compound

HRID 1619046Notes

Reaction equation

HRID 1619046 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

7

Reactant 4

HCID 8857Ethyl AcetateHCID 664601,1,3,3-TetramethylguanidineHCID 5834662-Chloro-5-fluoropyrimidineHCID 89832293HCID 89832293, compound

Product 1

HCID 89832319HCID 89832319, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-21f89632496c43ca9918fda90d35137b
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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