Methanol → HCID 67028534, compound

HRID 2066152Notes

Reaction equation

HRID 2066152 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][C@@H:11]2[CH3:29])=[O:9])=[CH:4][CH:3]=1.[CH2:30]([NH2:32])[CH3:31].CO>>[ClH:1].[CH2:30]([NH:32][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][C@@H:11]2[CH3:29])=[O:9])=[CH:6][N:7]=1)[CH3:31]

Participants

4

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 59161366(2S)-1-[(6-Chloro-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

Product 1

HCID 67028534HCID 67028534, compound

Conditions

Temperature
120 °C

Procedure

(2S)-1-[(6-Chloro-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 26) (67 mg, 0.15 mmol) was weighed into a microwave vial, and treated with ethylamine, 2.0M in methanol (1.5 ml, 3.0 mmol). The clear solution was heated in the microwave to 120° C. for 18 h with stirring. LCMS analysis showed complete conversion. 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 colourless gum (59 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude material as a yellow gum (76 mg)
  3. customThis was purified by MDAP

Sources & evidence

ORD record
ord-48ba170a59634092b007afc1a082dac0
Source dataset
uspto-grants-2012_10
Patent number
US08288388B2

Reaction notes

Loading…