Water → HCID 67537701, compound

HRID 1496637Notes

Reaction equation

HRID 1496637 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[S:19][C:18]([CH2:20][CH3:21])=[N:17][C:16]=3[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:5]1([N:8]([C:9]2[CH:14]=[C:13]([C:15]3[S:19][C:18]([CH2:20][CH3:21])=[N:17][C:16]=3[C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH:12]=[CH:11][N:10]=2)[C:1](=[O:3])[CH3:2])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 67436467HCID 67436467, compound

Product 1

HCID 67537701HCID 67537701, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At 40° C., 35 mg (0.44) mmol of acetyl chloride are added dropwise to a solution of 100 mg (0.29 mmol) of N-cyclopropyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine and 80 mg (0.58 mmol) of potassium carbonate in 5 ml acetonitrile. After 4 h, 30 ml of water are added, and the reaction mixture is extracted with ethyl acetate (3×25 ml). The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 39 mg (31%) of the desired product; 1H-NMR(MeCN-d3) δ: 8.40 (d, 1H), 7.49 (m, 2H), 7.16 (d, 1H), 7.108 (m, 3H), 3.05 (q, 2H), 2.99 (m, 1H), 2.07 (s, 3H), 1.40 (t, 3H), 0.79 (m, 2H), 0.44 (m, 2H).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. customThe residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-fef5311ffad94020b4012339f096a7b0
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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