Hydrochloric Acid → HCID 178456072, compound

HRID 980240Notes

Reaction equation

HRID 980240 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]([C:12]1[C:21]([C:22]([NH:24][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[O:23])=[C:20]([OH:30])[C:19]2[C:14](=[C:15]([C:31]([F:34])([F:33])[F:32])[CH:16]=[CH:17][CH:18]=2)[N:13]=1)[CH2:10][CH3:11].N1C=CC=CC=1.Cl>O>[C:1]([NH:8][C@H:9]([C:12]1[C:21]([C:22]([NH:24][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[O:23])=[C:20]([OH:30])[C:19]2[C:14](=[C:15]([C:31]([F:33])([F:32])[F:34])[CH:16]=[CH:17][CH:18]=2)[N:13]=1)[CH2:10][CH3:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178456063HCID 178456063, compound

Product 1

HCID 178456072HCID 178456072, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of acetic anhydride and 6 g of 2-[(1S) 1-aminopropyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline carboxamide of Example 8 were added dropwise with stirring to 60 ml of pyridine and stirring was maintained for 90 minutes at ambient temperature. The solution was poured into 150 ml of iced water and concentrated hydrochloric acid was added until a pH of 1. The precipitate was filtered, washed with water and then dissolved in tetrahydrofuran. The organic phase was dried, and concentrated to dryness under reduced pressure. The residue was taken up in ether, filtered and dried under reduced pressure at 80° to obtain 5.3 g of 2-[(1S) 1-(acetylamino)-propyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline carboxamide melting at 275° C. and having a specific rotation of [α]D =+43.5°±4° (c=0.3% in DMF).

Workup

  1. additionwas added until a pH of 1
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dissolutiondissolved in tetrahydrofuran
  5. customThe organic phase was dried
  6. concentrationconcentrated to dryness under reduced pressure
  7. filtrationfiltered
  8. customdried under reduced pressure at 80°

Sources & evidence

ORD record
ord-0853cb25893e414dbe7d7409dfc34e46
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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