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(Dimethyl sulfide)trihydroboron → 4-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279089
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HRID 2279089 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:39]([CH3:40])=[N:38][N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:24][C:23]=3[F:36])[CH:21]=2)=O)[CH:10]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:24][C:23]=3[F:36])[N:19]=[C:18]3[N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[N:38]=[C:39]([CH3:40])[C:17]=23)[CH:10]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 900135244-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 900142534-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester수율 51.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 529 mg of 4-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester in 15 ml of dry THF 6 ml of borane-dimethylsulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for 30 min. The reaction was quenched by the addition of 3.75 ml of methanol, and the solvents were evaporated. The residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient) yielding 266 mg (51%) of the title compound.

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 30 min
  3. customThe reaction was quenched by the addition of 3.75 ml of methanol
  4. customthe solvents were evaporated
  5. customThe residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-9e93154d37e24e8a98124cc4fae3fe24
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133181B2

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