Dichloromethane → HCID 66707379, compound

HRID 911744Notes

Reaction equation

HRID 911744 reaction equation
C([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][CH2:22][CH2:23][N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]3=[O:33])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[C:34]([OH:40])([C:36](F)(F)F)=[O:35].Cl[CH2:42]Cl>>[C:6]([OH:5])(=[O:7])[CH2:42][CH2:36][C:34]([OH:40])=[O:35].[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[S:20][CH2:21][CH2:22][CH2:23][N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[NH:26][C:25]1=[O:33]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66707185HCID 66707185, compound

Product 1

HCID 66707379HCID 66707379, compoundYield 70%

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propylthio]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (209 mg, 0.396 mmol) in dichloromethane (10 mL), then add TFA (0.5 mL) dropwise and stir at room temperature overnight. Remove solvents in vacuo then free base using an SCX column, eluting with 7M ammonia in methanol. Concentrate in vacuo, then use a method similar to the General Procedure 2-1 and freeze dry to give the title compound as a solid (140 mg, 70%). MS (ES+) m/z: 388 (M+H)+.

Workup

  1. washeluting with 7M ammonia in methanol
  2. concentrationConcentrate in vacuo
  3. customdry

Sources & evidence

ORD record
ord-f3e0e49036484025b2df68b4e8b789f5
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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