Dichloromethane → HCID 68520566, compound

HRID 2242148Notes

Reaction equation

HRID 2242148 reaction equation
C(OC([N:8]1[C:12]([CH:13]2[CH2:16][CH:15]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH2:14]2)=[CH:11][C:10]([NH:25][C:26](=[O:36])[C:27]([CH3:35])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH3:28])=[N:9]1)=O)(C)(C)C.C(OC(N1C(NC(=O)C(C)(C2C=CC=CN=2)C)=CC(C2CC(OC(=O)NCC3CC3)C2)=N1)=O)(C)(C)C.C(Cl)Cl>C(O)(C(F)(F)F)=O.CCOC(C)=O>[CH3:35][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)([CH3:28])[C:26]([NH:25][C:10]1[CH:11]=[C:12]([CH:13]2[CH2:14][CH:15]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH2:16]2)[NH:8][N:9]=1)=[O:36]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 68521450HCID 68521450, compoundHCID 68521544HCID 68521544, compound

Product 1

HCID 68520566HCID 68520566, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(3-cyclopropylmethylcarbamoyloxy-cyclobutyl)-3-(2-methyl-2-pyridin-2-yl-propionylamino)-pyrazole-1-carboxylic acid tert-butyl ester and 3-(3-cyclopropylmethylcarbamoyloxy-cyclobutyl)-5-(2-methyl-2-pyridin-2-yl-propionylamino)-pyrazole-1-carboxylic acid tert-butyl ester (120 mg, prepared by procedures analogous to those described in Example 221, Steps A to E, using appropriate starting materials) was dissolved in TFA (0.19 mL) and CH2Cl2 (1.25 mL) at room temperature. After 4 h, the solution was diluted with EtOAc and the solution was washed sequentially with saturated aqueous NaHCO3 solution (2×), water, and saturated aqueous NaCl solution. The organic layer was dried over Na2SO4 and concentrated. Purification of the residue by silica gel chromatography afforded the title compound as a solid. MS (M+H)+=398.3.

Workup

  1. customprepared by procedures analogous to
  2. customat room temperature
  3. washthe solution was washed sequentially with saturated aqueous NaHCO3 solution (2×), water, and saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-6829e8f13b44474bb5ed4ee5f19333c2
Source dataset
uspto-grants-2010_03
Patent number
US07671072B2

Reaction notes

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