HCID 57595477, compound → HCID 57595476, compound

HRID 1786050Notes

Reaction equation

HRID 1786050 reaction equation
[C:1]([N:4]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[CH2:27][CH2:26][CH2:25][N:24]3C(OCC3C=CC=CC=3)=O)=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:38])[CH2:6]1)(=[O:3])[CH3:2]>Br.C(O)(=O)C>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([N:4]([C@H:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([CH:23]4[CH2:27][CH2:26][CH2:25][NH:24]4)=[CH:21][CH:22]=3)[C@@H:7]([CH3:38])[CH2:6]2)[C:1](=[O:3])[CH3:2])=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 57595477HCID 57595477, compound

Product 1

HCID 57595476HCID 57595476, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

Benzyl 2-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pyrrolidine-1-carboxylate (237 mg, 0.381 mmol) was dissolved in HBr/Acetic acid (5 mL) and stirred for 2 h. The reddish slurry was partitioned between Et2O and 1N HCl. The HCl/water layer was washed 3× with Et2O to rid the benzyl bromide. The water layer was neutralized with 1N NaOH, and washed 3× with methylene chloride. The organic layer was dried over MgSO4, filtered and concentrated to afford the title compound (170 mg, 91%) as a white solid. 1H-NMR (CDCl3) δ: 1.05-1.20 (m, 1H), 1.13 (s, 3H), 1.50-1.62 (m, 1H), 1.76-1.90 (m, 2H), 2.02 (s, 3H), 2.05-2.20 (m, 2H), 2.20-2.38 (m, 1H), 2.93-3.03 (m, 1H), 3.09-3.18 (m, 1H), 4.05 (t, 1H), 4.72-4.82 (m, 1H), 5.45-5.75 (m, 1H), 6.49 (d, 1H), 6.88 (t, 1H), 7.11-7.29 (m, 8H), 7.37 (d, 2H).

Workup

  1. customThe reddish slurry was partitioned between Et2O and 1N HCl
  2. washThe HCl/water layer was washed 3× with Et2O
  3. washwashed 3× with methylene chloride
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b8d38a654c4443819c1a1305a4ea8781
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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