Water → N-(3-(3-bromopyridin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amine

HRID 1846770Notes

Reaction equation

HRID 1846770 reaction equation
Cl.[Br:2][C:3]1[C:4]([O:9][CH:10]2[CH2:13][CH:12]([NH2:14])[CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.Cl[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[Br:2][C:3]1[C:4]([O:9][CH:10]2[CH2:11][CH:12]([NH:14][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:13]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 674787263-((3-Bromopyridin-2-yl)oxy)cyclobutanamine hydrochloride

Product 1

HCID 58548561N-(3-(3-bromopyridin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amineYield 60%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-((3-bromopyridin-2-yl)oxy)cyclobutanamine hydrochloride (242 mg, 1 mmol), 2-chloro-benzothiazole (169 mg, 1 mmol) and DIEA (286 mg, 2 mmol) in NMP (10 mL) was heated to 180° C. for 2 hours in microwave. The reaction mixture was added water, extracted with EtOAc (40 mL), washed with brine and dried over Na2SO4. The organic layers were concentrated and purified by column chromatography to give N-(3-((3-bromopyridin-2-yl)oxy)cyclobutyl)benzo[d]thiazol-2-amine (225 mg, 0.6 mmol, yield 60%). ESI-MS (M+1): 376 calc. for C16H14BrN3OS 375.

Workup

  1. extractionextracted with EtOAc (40 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-d646af6446424e1d8bb8d1728370f53e
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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