Methanol → HCID 67028739, compound

HRID 43419Notes

Reaction equation

HRID 43419 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@@H:12]2[CH3:30])=[O:10])=[CH:4][CH:3]=1.[CH2:31]([NH2:33])[CH3:32].CO>C(O)(C)C>[ClH:1].[CH2:31]([NH:33][C:2]1[CH:3]=[CH:4][C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@@H:12]2[CH3:30])=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:32]

Participants

5

Reactant 3

HCID 887Methanol3×HCID 6341Ethylamine3×HCID 59161377(2S)-1-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

Product 1

HCID 67028739HCID 67028739, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

(2S)-1-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 24) (67 mg, 0.15 mmol) was weighed into a microwave vial, and dissolved in isopropanol (0.7 ml). Ethylamine, 2.0M in methanol (1.5 ml, 3.0 mmol) was added, and the clear solution was heated in the microwave to 120° C. for 6 h with stirring. LCMS analysis showed <20% conversion. The mixture was treated with further ethylamine, 2.0M in methanol (0.75 ml, 1.50 mmol) and returned to the microwave for 18 h at 120° C. with stirring. LCMS analysis showed ˜50% conversion. The reaction mixture was treated with further ethylamine, 2.0M in methanol (1.5 ml, 3.0 mmol), and again heated in the microwave for 18 h at 120° C. with stirring. LCMS now showed adequate conversion, >65%. The reaction mixture was concentrated to give the crude material as a yellow gum (76 mg). This was purified by MDAP to give the free base of the title compound as a pale yellow gum (34 mg).

Workup

  1. stirringwith stirring
  2. temperatureagain heated in the microwave for 18 h at 120° C.
  3. stirringwith stirring
  4. concentrationThe reaction mixture was concentrated
  5. customto give the crude material as a yellow gum (76 mg)
  6. customThis was purified by MDAP

Sources & evidence

ORD record
ord-f766b604c7c94eaea4859e675810b028
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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