Ethyl Acetate → HCID 57725407, compound

HRID 1922258Notes

Reaction equation

HRID 1922258 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.C(OCC)(=O)C>CN1C(=O)CCC1>[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 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 5325951(S)-(+)-1-Cyclohexylethylamine

Product 1

HCID 57725407HCID 57725407, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To the 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, 20 mmol). The reaction solution was stirred at 110° C. for 96 hr. The reaction was worked up by adding 170 ml ethyl acetate and washed with 1×60 ml of saturated NaHCO3, 1×60 ml 5% NaHCO3 solution, 1×60 ml water, 1×60 ml saturated NaCl, dried with 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 1×60 ml of saturated NaHCO3, 1×60 ml 5% NaHCO3 solution, 1×60 ml water, 1×60 ml saturated NaCl
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d97fc62f6ea94b1d8d3633f3bcd65ccc
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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