Trifluoroacetic acid → HCID 49763930, compound

HRID 1893240Notes

Reaction equation

HRID 1893240 reaction equation
C([NH:5][C:6](=[O:41])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:23][CH:22]([NH:24][C:25]([CH2:27][NH:28][C:29](=[O:40])[C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=4)=[O:26])[CH2:21]3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>>[F:38][C:36]([F:37])([F:39])[C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[C:29]([NH:28][CH2:27][C:25](=[O:26])[NH:24][CH:22]1[CH2:21][N:20]([CH:17]2[CH2:16][CH2:15][CH:14]([C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:6]([NH2:5])=[O:41])=[CH:9][CH:10]=3)[CH2:19][CH2:18]2)[CH2:23]1)=[O:40]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49763929HCID 49763929, compound

Product 1

HCID 49763930HCID 49763930, compound

Procedure

N-[(1-{4-[4-(3-tert-Butyl-ureido)-phenyl]-cyclohexyl}-azetidin-3-ylcarbamoyl)-methyl]-3-trifluoromethyl-benzamide (prepared as described in Example 18, 50 mg, 0.087 mmol) was treated with TFA (1 mL) at room temperature overnight. The reaction was quenched with saturated NaHCO3. The reaction solution was extracted with a chloroform/IPA “cocktail” (˜3:1, v/v). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford two title compound as white solid.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionThe reaction solution was extracted with a chloroform/IPA “cocktail” (˜3:1
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas then purified by a CombiFlash® system

Sources & evidence

ORD record
ord-d27d197c6756454ea8e8c78bc0c61084
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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