Diisopropylethylamine → HCID 57725478, 화합물

HRID 2370558노트

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HRID 2370558 반응식
[Br:1][C:2]1[C:10]2[S:9][C:8](Cl)=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].Cl.[NH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[OH:22])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 23148836HCID 23148836, 화합물

생성물 1

HCID 57725478HCID 57725478, 화합물

시약·촉매·용매 2

HCID 13387N-methyl-2-pyrrolidone용매HCID 516892Sodium Bicarbonate용매

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온도
125 °C

실험 절차

To the solution of 7-bromo-2-chloro-6-methoxybenzo[d]thiazole (150 mg, 0.539 mmol, 1.0 eq) in 1 mL of NMP was added (1R,2R)-2-aminocyclohexanol hydrochloride (0.123 mg, 0.809 mmol, 1.5 eq) and DIPEA (263 μL, 1.503 mmol, 2.8 eq) at room temperature. The reaction mixture was stirred at 125° C. for 12 hours, thereafter the mixture was diluted with saturated sodium bicarbonate solution (ca. 100 mL) and aqueous layer extracted with ethyl acetate (ca. 200 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give crude product as brown oil which was sufficiently pure and was carried to next step without further purification. LC/MS (m/z) [359.0] (MH+)

후처리

  1. extractionextracted with ethyl acetate (ca. 200 mL×3)
  2. dry with materialCombined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customcondensed under reduced pressure
  5. customto give crude product as brown oil which
  6. customwas carried to next step without further purification

출처 및 근거

ORD 기록
ord-bfd8d07ec73a4883b9663cf764d875ac
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710048B2

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