Dichloromethane → HCID 178456063, compound

HRID 980230Notes

Reaction equation

HRID 980230 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C@@H:16]([NH:19]C(=O)OC(C)(C)C)[CH2:17][CH3:18])[C:3]=1[C:27]([NH:29][C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[O:28].C(Cl)Cl.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O.C(#N)C>[NH2:19][C@H:16]([C:4]1[C:3]([C:27]([NH:29][C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[O:28])=[C:2]([OH:1])[C:11]2[C:6](=[C:7]([C:12]([F:13])([F:15])[F:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 178456096HCID 178456096, compound

Product 1

HCID 178456063HCID 178456063, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6.5 g of the product of Example 7, 130 ml of methylene chloride and 65 ml of trifluoroacetic acid was stirred for 2 hours at ambient temperature and then the methylene chloride and trifluoroacetic acid were eliminated under reduced pressure. The residue was taken up in iced water and the pH was adjusted to 7 with a solution of sodium bicarbonate. The mixture was filtered and the product was washed and dried under reduced pressure at 100° C. The product obtained was dissolved at reflux in 120 ml of acetonitrile and the solution was filtered. The filtrate was concentrated to 100 ml and the crystals obtained were frozen, separated, washed and dried under reduced pressure at 100° C. to obtain 3.25 g of 2-[(S) 1-aminopropyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 206° C. and having a specific rotation of [α]D =+177°±2.5° (c=0.8% in CH3COOH).

Workup

  1. filtrationThe mixture was filtered
  2. washthe product was washed
  3. customdried under reduced pressure at 100° C
  4. customThe product obtained
  5. dissolutionwas dissolved
  6. filtrationthe solution was filtered
  7. concentrationThe filtrate was concentrated to 100 ml
  8. customthe crystals obtained
  9. temperaturewere frozen
  10. customseparated
  11. washwashed
  12. customdried under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-f6e633e424ac42c5952b99769e540b17
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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