1,2-Dichloroethane → HCID 57476548, compound

HRID 249996Notes

Reaction equation

HRID 249996 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(Cl)CCl.CCN(C(C)C)C(C)C>O1CCCC1.ClCCl.O>[N:21]1([C:18]([C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[S:10][C:11]=3[CH:17]=2)=[O:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 27567632-[(tert-Butoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylic acid

Product 1

HCID 57476548HCID 57476548, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

In a 250 ml flask was added 2-(tert-butoxycarbonyl-amino)benzo[d]thiazole-6-carboxylic acid (1.0 g, 3.4 mmol) and pyrrolidine (0.559 mL, 6.8 mmol) in tetrahydrofuran (50 mL). To this solution was added EDC (1.3 g, 6.8 mmol), 1-hydroxybenzotriaxole (1.041 g, 6.8 mmol) and Hunig's Base (2.37 mL, 13.59 mmol). The reaction was stirred at 25° C. for 1 hour. The reaction was then poured into water and dichloromethane. The water was extracted 3 times with dichloromethane and the organic layers were combined and concentrated. The residue was taken up in a small amount of dichloromethane and precipitated out with diethyl ether/hexanes. The flask was put in the freezer for 1 hour and filtered. The white precipitate was collected to yield tert-butyl 6-(pyrrolidine-1-carbonyl)benzo[d]thiazol-2-ylcarbamate (1.09 g, 3.14 mmol, 92% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.95 (s, 1 H), 8.14 (s, 1 H), 7.61-7.77 (m, J=8.39, 1.98 Hz, 1 H), 7.46-7.63 (m, 1 H), 3.39-3.63 (m, 4 H), 1.74-2.00 (m, 4 H), 1.45-1.62 (m, 9 H). MS (LC/MS) R.T.=3.40; [M+H]+=363.1.

Workup

  1. extractionThe water was extracted 3 times with dichloromethane
  2. concentrationconcentrated
  3. customprecipitated out with diethyl ether/hexanes
  4. waitThe flask was put in the freezer for 1 hour
  5. filtrationfiltered
  6. customThe white precipitate was collected

Sources & evidence

ORD record
ord-d3fd02e0217649f09697a98de0362b54
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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