HCID 86758100, compound → HCID 86756035, compound

HRID 1937473Notes

Reaction equation

HRID 1937473 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:19])=[CH:13][C:14]=2[N+:16]([O-])=O)[C@H:9]([N:20]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:8][C@@H:7]1[CH3:40])=[O:5])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:19])=[CH:13][C:14]=2[NH2:16])[C@H:9]([N:20]([CH2:25][C:26]2[CH:27]=[C:28]([C:36]([F:37])([F:38])[F:39])[CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:8][C@@H:7]1[CH3:40])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86758100HCID 86758100, compound

Product 1

HCID 86756035HCID 86756035, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-8-nitro-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 107) (0.747 g, 1.25 mmol), ethanol (20 mL), and 10% palladium on carbon (0.40 g) were combined and agitated under 36 psi of H2 on a Parr shaker for 2 h and 15 min. The mixture was then filtered through a bed of Celite®. The Celite® was washed with ethanol, and the filtrate was concentrated in vacuo. Purification by silica gel chromatography using 30-100% ethyl acetate/hexanes as eluent afforded 0.386 g (54%) of cis-8-amino-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester MS m/z 568 (M++H); 1H NMR (CDCl3) δ 7.8 (bs, 1H), 7.7 (bs, 1H), 7.65 (bs, 1H), 6.7 (bs, 1H), 6.38 (bs, 1H), 3.78 (s, 3H), and 0.161 g (24%) of cis-8-amino-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester MS m/z 534 (M++H); 1H NMR (CDCl3) δ 7.79 (bs, 1H), 7.7 (bs, 1H), 7.65 (bs, 1H), 7.02 (bt, 1H), 6.72 (bs, 1H), 6.4 (bd, 1H), 3.78 (s, 3H).

Workup

  1. filtrationThe mixture was then filtered through a bed of Celite®
  2. washThe Celite® was washed with ethanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-54823a604deb44b4a5579a069d2db6c1
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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