HCID 11611088, compound → HCID 10172419, compound

HRID 1987818Notes

Reaction equation

HRID 1987818 reaction equation
Cl.[O:2]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12][C:13]([C@@H:15]3[CH2:24][C:23]4[C:18](=[CH:19][C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:22]=4)[CH2:17][NH:16]3)=[O:14])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[O:2]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12][C:13]([C:15]3[N:16]=[CH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=4)=[O:14])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 11611088HCID 11611088, compound

Product 1

HCID 10172419HCID 10172419, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

(The title product was prepared according to the procedure of E. D. Cox; T. J. Hagen; R. M. McKernan; J. M. Cook, Med. Chem. Rest. 1995, 5, 710-718). To a solution of (3S)-7-tert-butyl-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide hydrochloride, Example 10(d), (80 mg, 0.219 mmol) in toluene (10 mL) was added manganese dioxide (110 mg, 1.1 mmol). The reaction mixture was stirred at 70° C. under N2 for 1.5 h, filtered through a pad of Celite®, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (8:1 hexane/EtOAc) to give the title compound as an yellow solid. Mp 154-157° C. MS (ESI, pos. ion) m/z: 363 (M+1).

Workup

  1. custom(The title product was prepared
  2. filtrationfiltered through a pad of Celite®
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (8:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-9acad713827842a18c2352276d0d9560
Source dataset
uspto-grants-2009_06
Patent number
US07553848B2

Reaction notes

Loading…