2-Chlorobenzothiazole → HCID 178454112, compound

HRID 707263Notes

Reaction equation

HRID 707263 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH:12][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 178454110HCID 178454110, compound

Product 1

HCID 178454112HCID 178454112, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of tert-butyl(cis-3-aminocyclobutyl)carbamate (1.26 g, 6.77 mmol), 2-chlorobenzothiazole (0.965 mL, 6.77 mmol) and N,N-diisopropylethylamine (2.354 mL, 13.53 mmol) in DMSO (5 mL) was heated to 110° C. in a sealed microwave vial for 4 h, cooled to room temperature, diluted with water and extracted with EtOAc. EtOAc extract was concentrated and crude material purified with ISCO using silica gel column eluting with 0-80% EtOAc/hexane to give the desired product tert-butyl(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)carbamate (1.5 g, 4.70 mmol, 69.4% yield). m/z: 320.1 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionEtOAc extract
  4. concentrationwas concentrated
  5. customcrude material purified with ISCO
  6. washeluting with 0-80% EtOAc/hexane

Sources & evidence

ORD record
ord-7e8bb65403b54011a99136f7c119d068
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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