Hydrochloric Acid → HCID 57619388, compound

HRID 1754736Notes

Reaction equation

HRID 1754736 reaction equation
C(OC(=O)[N:7]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:8]1[S:9][C:10]([C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])=[CH:11][N:12]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>ClCCl>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][NH:7][C:8]2[S:9][C:10]([C:13]([C:15]3[C:23]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)=[O:14])=[CH:11][N:12]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57619372HCID 57619372, compound

Product 1

HCID 57619388HCID 57619388, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-fluoro-benzyl)-[5-(1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (549, 0.11 g, 0.2 mmol) in dichloromethane (2 mL) was added hydrogen chloride (4 M in 1,4-dioxane, 2 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into cold sodium bicarbonate solution, extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. After removal of solvents, the residue was washed with ethyl acetate to provide the desired compound as a yellow solid (P-0177, 9 mg, 10%). MS (ESI) [M+H+]+=353.12.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of solvents
  5. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-9a0a44c504ce4491b1c0a7feee4529dc
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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