Hydrochloric Acid → [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone

HRID 2119607Notes

Reaction equation

HRID 2119607 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[S:13][C:14]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:15][N:16]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)C>[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[S:13][C:14]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[O:25])=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20616905{3-[5-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic Acid tert-butyl Ester

Product 1

HCID 23442548[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanoneYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

900 mg {3-[5-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic acid tert-butyl ester was dissolved in diethyl ether and hydrogen chloride in ether added dropwise with stirring. The mixture was stirred overnight at room temperature and poured into saturated aqueous sodium bicarbonate solution. The organics were extracted with dichloromethane (3×25 ml), dried over magnesium sulfate and evaporated under reduced pressure to afford [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone as a yellow gum (579 mg, 88%). A solution of 0.22 ml tert-butanol in hexane (2 ml) was cautiously added to a stirred solution of 0.2 ml chlorosulfonyl isocyanate in hexane (5 ml). The resulting white precipitate was stirred until it had dissolved (1.5 h) and the mixture cooled to −78° C. before the slow addition of a solution of [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone and 0.4 ml triethylamine in dichloromethane. The cooling bath was removed and the yellow mixture allowed to reach room temperature and stirred 2 h at room temperature. The mixture was poured into water and the organics extracted with ethyl acetate (2×25 ml). The combined organics were washed with brine, dried over magnesium sulfate and evaporated. The resulting oil was purified by column chromatography on silica gel (150 g, 2:1 ethyl acetate/hexane) to afford the title compound (241 mg, 24%) as a pale yellow oil. MS (m/e): 409.3 (M−H, 100%)

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionThe organics were extracted with dichloromethane (3×25 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fb9ddc81fce643beae1a59960471785f
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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