Diisopropylethylamine → HCID 57725706, 화합물

HRID 1988453노트

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HRID 1988453 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 57725706HCID 57725706, 화합물수율 76.2%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
115 °C

실험 절차

To the 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 prep HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with ethyl acetate (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+).

후처리

  1. customThe crude reaction solution
  2. customwas purified by prep HPLC
  3. customto give
  4. custompurified fractions that
  5. extractionThe resulting solution was extracted with ethyl acetate (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

출처 및 근거

ORD 기록
ord-0cb7c488e14e41f49f4e45b377ba6095
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553854B2

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