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Bromo tert-butylacetate → {4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl}-acetic acid tert-butyl ester

HRID 45073
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HRID 45073 반응식
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[C:23]5[CH2:31][CH2:30][NH:29][CH2:28][C:24]=5[N:25]=[CH:26][N:27]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.C([CH2:38][C:39]([O:41]Br)=[O:40])(C)(C)C>C(#N)C>[C:3]([O:41][C:39](=[O:40])[CH2:38][N:29]1[CH2:30][CH2:31][C:23]2[C:22]([O:21][C:17]3[CH:16]=[C:15]4[C:20](=[CH:19][CH:18]=3)[N:12]([C:10](=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:4]=3)[CH:13]=[CH:14]4)=[N:27][CH:26]=[N:25][C:24]=2[CH2:28]1)([CH3:4])([CH3:8])[CH3:2]
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참가 물질

4

반응물 2

HCID 22013197Bromo tert-butylacetateHCID 462242625-(5,6,7,8-Tetrahydro-pyrido[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

생성물 1

HCID 59394435{4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl}-acetic acid tert-butyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 5-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide, Example 33-C, (250 mg, 0.55 mmol), bromo tert-butylacetate (204 μL, 1.38 mmol), TEA (384 μL, 2.76 mmol) and ACN (5 mL) is stirred at room temperature. Following completion of the reaction the contents of the flask are partitioned between DCM and brine. Organic layer is dried over anhydrous Na2SO4, concentrated, and the residue is separated via FCC (50-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 568.1 (M+1).

후처리

  1. customcompletion of the reaction the contents of the flask
  2. customare partitioned between DCM and brine
  3. dry with materialOrganic layer is dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customthe residue is separated via FCC (50-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-03202f1d9ca342bbb0c29f2a0dd307b8
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541432B2

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