Hydrochloric Acid → HCID 86756018, compound

HRID 382344Notes

Reaction equation

HRID 382344 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[C:13]=3[CH:14]=2)[C@H:9]([N:26]([CH2:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=2)[C:27]([O:29][CH3:30])=[O:28])[CH2:8][C@@H:7]1[CH3:46])=[O:5])[CH3:2].Cl>O1CCOCC1>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][NH:16][C:13]=3[CH:14]=2)[C@H:9]([N:26]([CH2:31][C:32]2[CH:33]=[C:34]([C:42]([F:43])([F:44])[F:45])[CH:35]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:37]=2)[C:27]([O:29][CH3:30])=[O:28])[CH2:8][C@@H:7]1[CH3:46])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86756019HCID 86756019, compound

Product 1

HCID 86756018HCID 86756018, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To an ice-cold solution of cis-5-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-methyl-2,3,6,7-tetrahydro-5H-pyrrolo[3,2-g]quinoline-1,8-dicarboxylic acid 1-tert-butyl ester 8-ethyl ester (Example 11) (200 mg) in 10 ml anhydrous dioxane was added 4M HCl in dioxane (15 ml) and the resulting solution was stirred for 18 h at room temperature. The solution was concentrated in vacuo. The residue was diluted with dichloromethane and washed twice with a saturated sodium bicarbonate solution. The organic phase was dried (MgSO4), filtered and concentrated. The crude product was chromatographed (50% ethyl acetate:hexane) to afford the title product (100 mg). MS m/z 559.3 (M+); 1H NMR (CDCl3) δ1.1 (d, 3H), 3.0 (t, 2H), 3.6 (t, 2H), 3.8 (s, 3H), 6.6 (s, 1H), 6.9 (s, 1H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with a saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (50% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-0cb82a4efac1478d9a94d776bf0a6b01
Source dataset
uspto-grants-2001_10
Patent number
US06310075B1

Reaction notes

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