Hydrochloric Acid → HCID 19785553, compound

HRID 256773

Reaction equation

HRID 256773 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:18][CH3:19])[S:13][C:14]=2[C:15](O)=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:38][OH:39].C(N(CC)CC)C.S1C=CN=C1C(O)=O.Cl>C(Cl)Cl.O.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:18][CH3:19])[S:13][C:14]=2[C:15]([NH:38][OH:39])=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 27627331,3-Thiazole-2-carboxylic acidHCID 197855604-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid

Product 1

HCID 19785553HCID 19785553, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled and stirred solution of 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid (5.00 g, 14.0 mmoles) and dimethylformamide (1.03 g, 14.1 mmoles) in methylene chloride (200 ml) was added dropwise oxalyl chloride (3.93 g, 31.0 mmoles) and the mixture was stirred for 40 minutes. On the other hand, hydroxylamine hydrochloride (3.91 g, 56.3 mmoles) in water (5 ml) and triethylamine (8.55 g, 84.5 mmoles) were dissolved in tetrahydrofuran (100 ml), and to the mixture was added dropwise the above-mentioned reacted solution of thiazolecarboxylic acid. After stirring for 30 minutes, the reaction mixture was acidified to pH 4 with 1M hydrochloric acid and extracted with methylene chloride. The organic layer was washed with water, dried and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the desired 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarbohydroxamic acid (2.50 g, 6.73 mmoles, 48%) as a light brown amorphous product.

Workup

  1. stirringAfter stirring for 30 minutes
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bda1daba9d21467684c7ef2c7cc1ca2f
Source dataset
uspto-grants-1993_11
Patent number
US05258396

Linked notes

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