Acetic Acid → HCID 59787347, compound

HRID 1965977Notes

Reaction equation

HRID 1965977 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:20]#[C:21][C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][CH2:21][C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59787364HCID 59787364, compound

Product 1

HCID 59787347HCID 59787347, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add a solution of 3-tert-butoxycarbonyl-7-chloro-6-(thiazol-2-ylethynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (160 mg, 0.41 mmol) in ethanol (10 mL) to a suspension of 10% Pd/C (Degussa type E101, 160 mg), then acetic acid (0.5 mL). Hydrogenate for 7 h (68-70 psi) then filter the catalyst through Celite® and concentrate in vacuo. Purify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 40 min) to obtain the desired intermediate (16 mg, 10%). MS (ES+) m/z: 393 (M+H)+.

Workup

  1. filtrationHydrogenate for 7 h (68-70 psi) then filter the catalyst through Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 40 min)

Sources & evidence

ORD record
ord-817f0385d304471cac05ddbf434e2c18
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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