Hydrochloric Acid → HCID 86756018, compound

HRID 1857457Notes

Reaction equation

HRID 1857457 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-5753224df74245078d0a598d8372e0e4
Source dataset
uspto-grants-2000_11
Patent number
US06147089

Reaction notes

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