Diisopropylethylamine → HCID 57725407, compound

HRID 2067179Notes

Reaction equation

HRID 2067179 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:13]1([C@@H:19]([NH2:21])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[CH:13]1([C@@H:19]([NH:21][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 5325951(S)-(+)-1-Cyclohexylethylamine

Product 1

HCID 57725407HCID 57725407, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloro-6-methoxybenzo[d]thiazole (2.0 g, 10 mmol) in 10 mL of NMP was added (S)-1-cyclohexylethanamine (2.3 g, 18 mmol) and DIPEA (3.5 mL, mmol). The reaction solution was stirred at 110° C. for 96 hours. The reaction was diluted with EtOAc (170 mL) and washed with saturated NaHCO3 (60 mL), 5% NaHCO3 solution (60 mL), water (60 mL), saturated NaCl (60 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give (S)—N-(1-cyclohexylethyl)-6-methoxybenzo[d]thiazol-2-amine as crude solid (3.39 grams). ES/MS m/z 291.1 (MH+).

Workup

  1. washwashed with saturated NaHCO3 (60 mL), 5% NaHCO3 solution (60 mL), water (60 mL), saturated NaCl (60 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50fe3681a676455a94eca9a984cd55d3
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

Loading…