Hydrochloric Acid → HCID 56646651, compound

HRID 872344Notes

Reaction equation

HRID 872344 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]4[C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1>CO.C(Cl)Cl>[C:27]1([C:26]2[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[N:19][C:18]=2[C:15]2[CH:14]=[CH:13][C:12]([C:8]3([NH2:7])[CH2:11][CH2:10][CH2:9]3)=[CH:17][CH:16]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 56954770HCID 56954770, compound

Product 1

HCID 56646651HCID 56646651, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[4-(3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg, 0.11 mmol) in MeOH (0.45 mL) and CH2Cl2 (0.75 mL) was added a 4 molar solution of HCl in dioxane (0.57 mL, 2.2 mmol, 20 5equiv). The resulting solution was stirred at room temperature for 12 h, then was concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 10 g SNAP cartridge: 100% CH2Cl2 4.0 min., gradient to 95% CH2Cl2/5% MeOH 9.5 min., gradient to 90% CH2Cl2/10% MeOH 6.1 min.) to give 1-[4-(3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (18 mg, 47%):

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe remaining material was purified
  3. customMPLC (Biotage Isolera; 10 g SNAP cartridge: 100% CH2Cl2 4.0 min., gradient to 95% CH2Cl2/5% MeOH 9.5 min., gradient to 90% CH2Cl2/10% MeOH 6.1 min.)

Sources & evidence

ORD record
ord-9994a9252364429db720550d221984e6
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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