Thionyl Chloride → HCID 86756022, compound

HRID 1937465Notes

Reaction equation

HRID 1937465 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:18]([OH:20])=O)=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([N:21]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[C:22]([O:24][CH3:25])=[O:23])[CH2:8][C@@H:7]1[CH3:41])=[O:5])[CH3:2].O=S(Cl)Cl.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH2:50]>ClCCl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:18](=[O:20])[NH:50][CH2:49][CH2:48][N:47]([CH3:51])[CH3:46])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([N:21]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:38])([F:40])[F:39])[CH:28]=2)[C:22]([O:24][CH3:25])=[O:23])[CH2:8][C@@H:7]1[CH3:41])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 86756023HCID 86756023, compound

Product 1

HCID 86756022HCID 86756022, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1,6-dicarboxylic acid 1-ethyl ester (Example 60) (75 mg, 1.26 mmol) and 1.5 ml SOCl2 was heated at reflux for 1.5 h. The cooled solution was evaporated to dryness and the residue dried under high vacuum for 30 min. The residue was diluted with 0.75 ml dichloromethane, and triethylamine (0.021 ml) and N,N-dimethyl ethylenediamine (11 mg, 1.26 mmol) were added sequentially. After 1.5 h, the reaction mixture was concentrated and the residue was chromatographed (5% MeOH-dichloromethane) to afford the desired product (72 mg (86%). MS m/z 663 (M++1); 1H NMR (CDCl3) δ 3.75 (s, 3H), 7.22 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. customThe cooled solution was evaporated to dryness
  4. customthe residue dried under high vacuum for 30 min
  5. additionwere added sequentially
  6. concentrationthe reaction mixture was concentrated
  7. customthe residue was chromatographed (5% MeOH-dichloromethane)

Sources & evidence

ORD record
ord-ada7013cc0d9462ca09a8b890b4703ca
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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