Diisopropylethylamine → (R,R)-2-Methyl-propane-2-sulfinic acid [2-[6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-1-(4-fluoro-phenyl)-ethyl]-amide

HRID 1400016Notes

Reaction equation

HRID 1400016 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[C:10]([Cl:18])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:19][CH2:20][C@H:21]([NH:29][S@@:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:18][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:20][C@H:21]([NH:29][S@@:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH:7]=2)[CH:13]=[CH:12][C:11]=1[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 249021774-Chloro-6-(3-chloro-4-trifluoromethyl-phenyl)pyrimidineHCID 66957899(R,R)-2-methyl-propane-2-sulfinic acid [2-amino-1-(4-fluoro-phenyl)-ethyl]-amide

Product 1

HCID 66957911(R,R)-2-Methyl-propane-2-sulfinic acid [2-[6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-1-(4-fluoro-phenyl)-ethyl]-amideYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidine (0.200 g, 0.68 mmol), (R,R)-2-methyl-propane-2-sulfinic acid [2-amino-1-(4-fluoro-phenyl)-ethyl]-amide (0.720 g, 2.79 mmol) and DIPEA (0.18 mL, 1.02 mmol) in DMF (5 mL) was heated at 80° C. for 16 h. The reaction mixture was cooled to rt, diluted with EtOAc (20 mL) and washed with NaCl (sat. aq., 2×30 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified (FCC) to give the title compound (0.172 g, 50%) as a yellow solid. MS (ESI+): calcd for C23H23ClF4N4OS m/z 514.12. found 515.1 (M+H)+.

Workup

  1. washwashed with NaCl (sat. aq., 2×30 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-cfbabb57fe1f44b0b69e8dec0067a039
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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