Dichloromethane → HCID 67398538, compound

HRID 914494Notes

Reaction equation

HRID 914494 reaction equation
C([O:5][C:6](=[O:40])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:32]2[N:37]=[CH:36][C:35]([CH2:38][CH3:39])=[CH:34][N:33]=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)=[CH:22][CH:21]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O.[Cl:48]CCl>>[ClH:48].[CH2:38]([C:35]1[CH:36]=[N:37][C:32]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:40])=[O:5])[S:12][CH:13]=2)=[N:33][CH:34]=1)[CH3:39]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59759191HCID 59759191, compound

Product 1

HCID 67398538HCID 67398538, compound

Procedure

2-[(4-{2-[(5-Ethylpyrimidin-2-yl)(4-pyrazin-2-ylbenzyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (180 mg) obtained in Example 403-1 was dissolved in dichloromethane (6 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; dichloromethane:methanol=10:1). The obtained compound was dissolved in diethyl ether (5 mL), hydrochloric acid-ethyl acetate (4 mol/L, 1 mL) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration to give the title compound (140 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; dichloromethane:methanol=10:1)
  3. dissolutionThe obtained compound was dissolved in diethyl ether (5 mL)
  4. additionhydrochloric acid-ethyl acetate (4 mol/L, 1 mL) was added
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-250fe64af1db4f27acae84bd8257e7a6
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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