Water → HCID 178519030, compound

HRID 496276Notes

Reaction equation

HRID 496276 reaction equation
Cl[C:2]1[NH:11][C:5]2=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=[C:4]2[N:3]=1.[NH:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1.O>CN1C(=O)CCC1>[Cl:10][C:7]1[N:6]=[C:5]2[NH:11][C:2]([N:12]3[CH2:17][CH2:16][C:15]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19](=[O:26])[O:18]4)[CH2:14][CH2:13]3)=[N:3][C:4]2=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 178477886HCID 178477886, compound

Product 1

HCID 178519030HCID 178519030, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 2,5-dichloro-3H-imidazo[4,5-b]pyridine (0.07 g, 0.37 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (0.15 g, 0.74 mmol) in dry NMP (3 mL) at 100° C. for 14 hours. Pour the cooled mixture into water (10 mL) and extract twice with EtOAc (10 mL). Wash the combined extracts with brine (10 mL), dry, and evaporate in vacuo. Purify by preparative TLC (5% MeOH—CH2Cl2) to obtain 1′-(5-chloro-3H-imidazo[4,5-b]pyridine-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a white solid.

Workup

  1. extractionextract twice with EtOAc (10 mL)
  2. washWash the combined extracts with brine (10 mL)
  3. customdry
  4. customevaporate in vacuo
  5. customPurify by preparative TLC (5% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-932f0439dcf149038038e3e4c932daa9
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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