Trifluoroacetic acid → HCID 90220400, compound

HRID 2199784Notes

Reaction equation

HRID 2199784 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[S:15][C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([C:19](=[O:21])[NH2:20])[N:18]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[S:15][C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([C:19]([NH2:20])=[O:21])[N:18]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90220485HCID 90220485, compound

Product 1

HCID 90220400HCID 90220400, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of {1-[4-carbamoyl-5-(pyridin-2-ylamino)-thiazol-2-yl]-piperidin-3-yl}-carbamic acid tert-butyl ester (prepared as described in example 1) (359 mg, 0.86 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL, 130 mmol) to form a yellow solution. The mixture was stirred at ambient temperature for 30 minutes then evaporated to dryness in vacuo. The residue was taken up in dichloromethane (25 mL) and washed with saturated aqueous sodium hydrogen carbonate (100 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (5×20 mL) until no further yellow color was extracted in to the organic layer. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give 2-((R)-3-amino-piperidin-1-yl)-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid amide as a yellow solid (280 mg).

Workup

  1. customto form a yellow solution
  2. customthen evaporated to dryness in vacuo
  3. washwashed with saturated aqueous sodium hydrogen carbonate (100 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane (5×20 mL) until no further yellow color
  6. extractionwas extracted in to the organic layer
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c75653b606543cf856fd8843f261380
Source dataset
uspto-grants-2016_06
Patent number
US09359345B2

Reaction notes

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