Sodium borohydride → Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712322노트

반응식

HRID 712322 반응식
[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]([CH:19]=[O:20])=[CH:17][C:16]([C:21]4[CH:22]=[N:23][C:24]([N:27]5[CH2:32][CH2:31][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:29][CH2:28]5)=[N:25][CH:26]=4)=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:39])[CH3:2].[BH4-].[Na+]>CCO.C(Cl)Cl.CCOC(C)=O>[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]([CH2:19][OH:20])=[CH:17][C:16]([C:21]4[CH:22]=[N:23][C:24]([N:27]5[CH2:28][CH2:29][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:32]5)=[N:25][CH:26]=4)=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:39])[CH3:2]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 86664036Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

생성물 1

HCID 66977202Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate수율 86%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21584144Dichloromethane ethanol용매

반응 조건

온도
0 °C

실험 절차

Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (560 mg, 1.02 mmol) was dissolved in 1:1 EtOH/CH2Cl2 (40 mL) and cooled to 0° C. NaBH4 (77 mg, 2.03 mmol) was added and the mixture allowed to warm to rt with stirring for 2 h. The mixture was diluted with EtOAc (200 mL), washed with water, brine and separated. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure to afford the desired compound (484 mg, 86%) as a white solid. MS: 554.12 [M+H]+.

후처리

  1. temperatureto warm to rt
  2. washwashed with water, brine
  3. customseparated
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aa98f7b42fa240f8aaff7faed3ac20a9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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