N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide → HCID 57853873, compound

HRID 1687279Notes

Reaction equation

HRID 1687279 reaction equation
Cl[C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][C:7](=[O:17])[C:6]=2[C:5]([O:18][CH3:19])=[C:4]([N+:20]([O-])=O)[CH:3]=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[NH2:20][C:4]1[CH:3]=[CH:2][C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][C:7](=[O:17])[C:6]=2[C:5]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 57853797N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 57853873HCID 57853873, compoundYield 133.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

632 g) N—((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide (100 mg, 0.3 mmol), 20% Pd(OH)2/C (30 mg) and Methanol (20 mL) were placed under a blanket of Hydrogen at atmospheric pressure. After 24 h the reaction mixture was filtered and the filtrate concentrated under reduced pressure to yield 105 mg (100%) of N—((S)-2-Amino-1-methoxy-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide; hydrochloride. TLC: 5:1 CH2Cl2:MeOH Rf 0.5 homogeneous; (SM A: Rf 0.55); 1H NMR (400 MHz, DMSO-d6) δ 7.98 (d, J=8.09 Hz, 1H), 7.01 (m, 1H), 6.86 (d, J=8.09 Hz, 1H), 3.95 (m, 1H), 3.66 (s, 3H), 3.5 (bs, water+NH2), 2.79-2.64 (m, 4H), 1.95-1.85 (m, 1H), 1.78 (s, 3H), 1.7-1.6 (m, 1H).

Workup

  1. filtrationAfter 24 h the reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bdbe07ffe8b4c14850e0fae6a36a048
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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