Water → HCID 178519031, compound

HRID 413256Notes

Reaction equation

HRID 413256 reaction equation
Cl[C:2]1[NH:14][C:5]2=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]2[N:3]=1.[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[O:21]2)[CH2:17][CH2:16]1.O>CN1C(=O)CCC1>[F:11][C:10]([F:13])([F:12])[C:8]1[CH:9]=[C:4]2[N:3]=[C:2]([N:15]3[CH2:20][CH2:19][C:18]4([C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:22](=[O:29])[O:21]4)[CH2:17][CH2:16]3)[NH:14][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 178506240HCID 178506240, compound

Product 1

HCID 178519031HCID 178519031, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 2-chloro-6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine (0.1 g, 0.45 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (0.2 g, 0.90 mmol) in dry NMP (5 mL) at 100° C. for 10 hours. Pour the cooled mixture into water (20 mL) and extract twice with EtOAc (20 mL). Wash the combined extracts with brine (20 mL), dry, and evaporate in vacuo. Purify by preparative TLC (4% MeOH-CH2Cl2) to obtain 1′-(6-trifluoromethyl-3-H-imidazo[4,5-b]pyridine-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a yellow solid.

Workup

  1. extractionextract twice with EtOAc (20 mL)
  2. washWash the combined extracts with brine (20 mL)
  3. customdry
  4. customevaporate in vacuo
  5. customPurify by preparative TLC (4% MeOH-CH2Cl2)

Sources & evidence

ORD record
ord-6f550771e928437d803bf8025a52797f
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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