Hydrochloric Acid → HCID 59828832, compound

HRID 1190944Notes

Reaction equation

HRID 1190944 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([CH3:32])OCC[O:28]2)=[CH:23][CH:22]=1.Cl>CO>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:3]2[C:4]3[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH2:7][CH2:6][C:5]=3[CH:17]=[CH:18][C:2]=2[Cl:1])=[CH:26][CH:25]=1)(=[O:28])[CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59828873HCID 59828873, compound

Product 1

HCID 59828832HCID 59828832, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 7-chloro-6-[4-(2-methyl-[1,3]dioxolan-2-yl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg, 0.32 mmol) in methanol (5 mL) and add 1N aqueous HCl (1 mL). Stir the solution at room temperature for 2 h. Remove the solvent, dissolve the residue in DCM and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1) to obtain the title compound as an oil (107 mg, 79%). GC-MS m/z: 424 (M+).

Workup

  1. customRemove the solvent
  2. dissolutiondissolve the residue in DCM
  3. washwash with saturated aqueous NaHCO3
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1)

Sources & evidence

ORD record
ord-dc203b743bc945f8a0172f3fdaee8bbc
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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