2-Chlorobenzothiazole → HCID 178420425, compound

HRID 1846792Notes

Reaction equation

HRID 1846792 reaction equation
C(N(C(C)C)C(C)C)C.Cl[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.[CH2:20]([O:27][CH:28]1[CH2:31][CH:30]([NH2:32])[CH2:29]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(N(C)C)=O.CCOC(C)=O>[S:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[NH:32][C@H:30]1[CH2:31][C@@H:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:29]1

Participants

6

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 12104169cis-3-(Benzyloxy)cyclobutanamine

Product 1

HCID 178420425HCID 178420425, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-ethyl-N-isopropylpropan-2-amine (3 g, 24 mmol), 2-chlorobenzo[d]thiazole (2.0 g, 12 mmol), and 3-benzyloxy-cyclobutylamine (2.08 g, 12 mmol) in DMA (20 mL) was heated to 130° C. for 20 h. Then it was cooled to RT and diluted with EtOAc (50 mL). The mixture was washed with water (2×25 mL), brine (25 mL), dried over MgSO4, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography (0 to 30% EtOAc/hexane gradient) to give two products as a white solid.

Workup

  1. temperatureThen it was cooled to RT
  2. washThe mixture was washed with water (2×25 mL), brine (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe oil was purified by silica gel chromatography (0 to 30% EtOAc/hexane gradient)
  8. customto give two products as a white solid

Sources & evidence

ORD record
ord-9fec738783294f3f9128ffc124e01474
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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