Pyridine → HCID 71657548, compound

HRID 591357Notes

Reaction equation

HRID 591357 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][C:22]4[CH2:23][NH:24][CH2:25][CH2:26][C:27]=4[N:28]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.C([O:38][CH2:39][C:40](Cl)=[O:41])(=O)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:12][CH2:13][N:14]([C:17]([NH:19][C:20]3[S:21][C:22]4[CH2:23][N:24]([C:39](=[O:38])[CH2:40][OH:41])[CH2:25][CH2:26][C:27]=4[N:28]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 71657445HCID 71657445, compound

Product 1

HCID 71657548HCID 71657548, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(6-fluoroindolin-1-yl)-N-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)piperidine-1-carboxamide, prepared as in Example 19 above (77.3 mg, 0.15 mmol) in CH2Cl2 (2 mL) was added pyridine (0.035 mL, 0.45 mmol, 3 equiv) and then acetoxyacetyl chloride (0.024 mL, 0.225 mmol, 1.5 equiv) at room temperature. The resulting mixture was stirred for 20 min and MeOH (2 mL) and K2CO3 (138 mg, 1.0 mmol) were added sequentially. The resulting mixture was stirred at room temperature for another 1 h. The resulting mixture was filtered and concentrated. The resulting residue was purified by column using 90-100% EtOAc/hexane as the eluent to yield an off-white solid.

Workup

  1. customat room temperature
  2. stirringThe resulting mixture was stirred at room temperature for another 1 h
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column
  6. customto yield an off-white solid

Sources & evidence

ORD record
ord-cb709cd31f4f467f81d43c94f4202be8
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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