Water → HCID 58548512, compound

HRID 1846818Notes

Reaction equation

HRID 1846818 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC[N:13]([CH:17]([CH3:19])[CH3:18])C(C)C.O.CN1[C:26](=[O:27])CCC1>>[CH2:19]1[CH:26]([OH:27])[CH2:18][CH:17]1[NH:13][C:2]1[S:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

5

Reactant 4

HCID 962WaterHCID 119872-ChlorobenzothiazoleHCID 13387N-methyl-2-pyrrolidoneHCID 81531Diisopropylethylamine

Product 1

HCID 58548512HCID 58548512, compoundYield 73%

Conditions

Temperature
180 °C

Procedure

A mixture of (1S,3S)-3-aminocyclobutanol hydrochloride (120 mg, 0.98 mmol, 1.0 eqv), 2-chloro-benzothiazole (purchased from ALDRICH™) (169 mg, 1 mmol, 1.02 eqv) and DIEA (286 mg, 2 mmol, 2.04 eqv) in NMP (2 mL) was heated to 180° C. for 2 hours in microwave. To the reaction mixture was added water, and the residue was extracted with EtOAc (30 mL). The combined organic layer was washed with brine and dried over Na2SO4. The organic layers were concentrated and purified by column chromatography on silica gel to give (1S,3S)-3-(benzo[d]thiazol-2-ylamino)cyclobutanol (160 mg, 0.72 mmol, yield 73%). ESI-MS (M+1): 221 calc. for C11H12N2OS 221.

Workup

  1. extractionthe residue was extracted with EtOAc (30 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-49f1ae679ebb4e15927cf50b35cd9fb4
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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