Diisopropylethylamine → HCID 57725706, compound

HRID 2067181Notes

Reaction equation

HRID 2067181 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.Cl.[NH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[OH:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]3[OH:21])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 57725706HCID 57725706, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-chloro-6-methoxybenzo[d]thiazole (1.0 g, 5 mmol) in 5.5 mL of NMP was added (1R,2R)-2-aminocyclohexanol hydrochloride (910 mg, 6 mmol) and DIPEA (2.44 mL, 14 mmol). The reaction solution was stirred at 115° C. for 96 hours. The crude reaction solution was purified by preparative HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with EtOAc (2×300 mL). The combined organic layers were washed with water (60 mL) and brine (60 mL), then dried over Na2SO4 and evaporated in vacuo to give (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) as an ivory solid. ES/MS m/z 279.1 (MH+).

Workup

  1. customThe crude reaction solution
  2. customwas purified by preparative HPLC
  3. customto give
  4. custompurified fractions that
  5. extractionThe resulting solution was extracted with EtOAc (2×300 mL)
  6. washThe combined organic layers were washed with water (60 mL) and brine (60 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3cf5d74336ad44d1a5e9a1171f80d1e2
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

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