HCID 67335805, compound → HCID 59822264, compound

HRID 1670574Notes

Reaction equation

HRID 1670574 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][S:21][C:22]3[NH:23][C:24]([CH3:27])=[N:25][CH:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[CH2:20][S:21][C:22]1[NH:23][C:24]([CH3:27])=[N:25][CH:26]=1

Participants

3

Reactant 1

HCID 67335805HCID 67335805, compound

Product 1

HCID 59822264HCID 59822264, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-(2-methyl-3H-imidazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (306 mg, 0.602 mmol) in methanol (20 mL) and bubble the resulting solution with hydrogen chloride gas for 5 min. Cap the flask and stir at room temperature overnight. Concentrate the mixture in vacuo. Purify the crude product by chromatography on silica gel (40 g) eluting with a step gradient of DCM/(chloroform:methanol:concentrated NH4OH) [100:0 (5 min), 19:1 (5 min), 9:1 (5 min), 4:1 (5 min), 3:2 (5 min), 1:1; flow rate: 28 mL/min] to provide 7-chloro-6-(2-methyl-3H-imidazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (193 mg, 100%). MS (ES+) m/z: 308 (M+H)+.

Workup

  1. custombubble the resulting solution with hydrogen chloride gas for 5 min
  2. customCap the flask
  3. concentrationConcentrate the mixture in vacuo
  4. customPurify the crude product by chromatography on silica gel (40 g)
  5. washeluting with a step gradient of DCM/(chloroform:methanol:concentrated NH4OH) [100:0 (5 min), 19:1 (5 min), 9:1 (5 min), 4:1 (5 min), 3:2 (5 min), 1:1; flow rate: 28 mL/min]

Sources & evidence

ORD record
ord-569d037295ea44e6ab70b650f7361c4c
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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