Hydrochloric Acid → (1R)-N2-[6-(3-Chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-1-(4-fluoro-phenyl)-ethane-1,2-diamine

HRID 1400017Notes

Reaction equation

HRID 1400017 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH:18][CH2:19][C@H:20]([NH:28][S@@](C(C)(C)C)=O)[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH:18][CH2:19][C@@H:20]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[NH2:28])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66957911(R,R)-2-Methyl-propane-2-sulfinic acid [2-[6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-1-(4-fluoro-phenyl)-ethyl]-amide

Product 1

HCID 51036598(1R)-N2-[6-(3-Chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-1-(4-fluoro-phenyl)-ethane-1,2-diamineYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R,R)-2-methyl-propane-2-sulfinic acid [2-[6-(3-chloro-4-trifluoromethyl-phenyl)-pyrimidin-4-ylamino]-1-(4-fluoro-phenyl)-ethyl]-amide (0.172 g, 0.337 mmol) in MeOH (5 mL) was added HCl (4 N in dioxane, 0.34 mL) at rt. After 30 min, the reaction mixture was purified directly via reverse phase chromatography. The desired fractions were then free-based by washing with sat. aq. NaHCO3 (2×30 mL) and extracting with EtOAc (2×25 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (75 mg, 54%) as a white solid. MS (ESI+): calcd for C19H15ClF4N4 m/z 410.09. found 411.1 (M+H)+. 1H NMR (CDCl3): 8.60 (s, 1H), 8.05 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.35 (dd, J=8.6, 5.3 Hz, 2H), 7.05 (t, J=8.6 Hz, 2H), 6.66 (s, 1H), 5.89 (s, 1H), 4.27 (s, 1H), 3.76-3.64 (m, 1H), 3.59-3.50 (m, 1H), 3.03-2.85 (m, 2H).

Workup

  1. customthe reaction mixture was purified directly via reverse phase chromatography
  2. washfree-based by washing with sat. aq. NaHCO3 (2×30 mL)
  3. extractionextracting with EtOAc (2×25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e204cb0bf4254d9ca92d5d2775e339d7
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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