Methanol → HCID 22710936, compound

HRID 352961Notes

Reaction equation

HRID 352961 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH3:33])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH:18]([C:34](=[O:45])[NH:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43]C)[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.B(Br)(Br)Br.ClCCl.CO.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH3:33])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH:18]([C:34](=[O:45])[NH:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[OH:43])[CH2:17]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 22277759Boron tribromide dichloromethaneHCID 22709920HCID 22709920, compound

Product 1

HCID 22710936HCID 22710936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (10 ml), 4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-[[N-(2-methoxybenzyl)]carbamoyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (195 mg) was dissolved, followed by the dropwise addition of a boron tribromide-dichloromethane solution (1.0M, 2.08 ml) at −78° C. The reaction mixture was heated to room temperature and stirred overnight. To the reaction mixture, methanol (2 ml), sodium carbonate (200 mg) and water (3 ml) were added to extract the organic layer, followed by drying over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The solid thus precipitated was collected by filtration while being washed with 1N hydrochloric acid, whereby the title compound (50 mg, 24%) was obtained as a pale yellow solid.

Workup

  1. extractionto extract the organic layer
  2. dry with materialby drying over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customThe solid thus precipitated
  5. filtrationwas collected by filtration
  6. washwhile being washed with 1N hydrochloric acid, whereby the title compound (50 mg, 24%)
  7. customwas obtained as a pale yellow solid

Sources & evidence

ORD record
ord-d8ad5d6f4b1b4b03b499228bec49c509
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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