Ammonia → HCID 71657442, compound

HRID 591352Notes

Reaction equation

HRID 591352 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][CH:22]=[C:23]([C:25]([O:27]CC)=O)[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[NH3:30]>CCO>[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][CH:22]=[C:23]([C:25]([NH2:30])=[O:27])[N:24]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 89612672HCID 89612672, compound

Product 1

HCID 71657442HCID 71657442, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
39 °C

Procedure

In a flask was placed ethyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazole-4-carboxylate (83.6 mg, 0.2 mmol) and EtOH (3 mL) was added. Then, NH3(aq) (24 mL) was added and the resulting mixture was heated to 38-40° C. for 24 h. The reaction did not go completion and another portion of NH3(aq) (24 mL) was added. The resulting mixture was stirred continuously at 38-40° C. for another 24 h. The resulting mixture was then concentrated to remove most of the solvent. The resulting white solid was filtered and washed with H2O (3 mL), 20% CH2Cl2/hexane (5 mL×2), then dried to yield as a white solid.

Workup

  1. customIn a flask was placed
  2. concentrationThe resulting mixture was then concentrated
  3. customto remove most of the solvent
  4. filtrationThe resulting white solid was filtered
  5. washwashed with H2O (3 mL), 20% CH2Cl2/hexane (5 mL×2)
  6. customdried
  7. customto yield as a white solid

Sources & evidence

ORD record
ord-4a5dc9b0bad1439da07404258828543b
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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