Diisopropylethylamine → N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide

HRID 38079

Reaction equation

HRID 38079 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)=[N:9][N:10]3[CH2:15][CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1.[F:23][C:24]([F:36])([F:35])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:16]3[CH:17]=[C:18]([NH:22][C:32](=[O:33])[CH2:31][C:28]4[CH:27]=[CH:26][C:25]([C:24]([F:35])([F:23])[F:36])=[CH:30][CH:29]=4)[CH:19]=[CH:20][CH:21]=3)=[N:9][N:10]3[CH2:15][CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 674228643-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine

Product 1

HCID 46701903N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine (prepared as described in Example 3) (100 mg, 0.324 mmol) in dichloromethane (8 mL), were added in the following order: (4-trifluoromethyl-phenyl)-acetic acid (132 mg, 0.648 mmol), DIPEA (125 mg, 166 uL, 0.972 mmol) and TBTU (312 mg, 0.972 mmol). The reaction mixture was stirred at room temperature for 3 hours. Then it was poured into a solution of saturated NaHCO3, the phases separated, and the organic phase was washed twice with saturated NaHCO3, and twice with water. The organic solvent was evaporated to dryness and the product was purified by flash chromatography over silica gel using dichloromethane-methanol (98:2) as the eluant system. N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide was obtained as a colorless solid (115 mg, 72%).

Workup

  1. customthe phases separated
  2. washthe organic phase was washed twice with saturated NaHCO3
  3. customThe organic solvent was evaporated to dryness
  4. customthe product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-83b629410a7b458f9d6afcb91300e00d
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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