Cyclopentyl isothiocyanate → 4-[2-(Cyclopentylamino)-1,3-thiazol-4-yl]benzoic acid

HRID 606608

Reaction equation

HRID 606608 reaction equation
N(C1CCCC1)=C=S.[CH:9]1([NH:14][C:15]([NH2:17])=[S:16])[CH2:13][CH2:12][CH2:11][CH2:10]1.Br[CH2:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=O>N.CO.C1COCC1>[CH:9]1([NH:14][C:15]2[S:16][CH:19]=[C:20]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)[N:17]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 141792Cyclopentyl isothiocyanateHCID 736945CyclopentylthioureaHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 598072964-[2-(Cyclopentylamino)-1,3-thiazol-4-yl]benzoic acid

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isothiocyanato-cyclopentane (4 g) in ammonia (37% in water, 8 mL) and methanol (32 mL) was stirred for 16 hours, filtered of and dried. The Cyclopentyl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=289.05 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Workup

  1. filtrationfiltered of and
  2. customdried
  3. temperaturewas heated to 80° C. for 2 hours
  4. temperatureThe mixture was then cooled to room temperature
  5. filtrationfiltered
  6. washThe solid was washed with a small amount of diethylether
  7. customdried
  8. customused in the next step without any further purification

Sources & evidence

ORD record
ord-646b3ae29c9346a8bf3197e800676313
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Linked notes

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