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Phosphorus oxide (P4O10) → 6-(5,5-Dimethyl-4,5-dihydrooxazol-2-yl)-N-(4-fluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40094
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HRID 40094 반응식
[F:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])=O)=[CH:16][CH:17]=3)[N:12]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[C:11]=2[CH:34]([CH3:36])[CH3:35])=[O:9])=[CH:4][CH:3]=1.C(N1C2C(=CC=C(C(NCC(O)(C)C)=O)C=2)C(C(NCC2C=CC(F)=C(F)C=2)=O)=C1C(C)C)C1C=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1C=CC=CC=1>[CH3:25][C:23]1([CH3:24])[O:26][C:19]([C:15]2[CH:14]=[C:13]3[C:18]([C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:38][CH:37]=4)=[O:9])=[C:11]([CH:34]([CH3:36])[CH3:35])[N:12]3[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:17][CH:16]=2)=[N:21][CH2:22]1
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참가 물질

5

반응물 3

HCID 14812Phosphorus oxide (P4O10)HCID 692261641-Benzyl-N3-(3,4-difluorobenzyl)-N6-(2-hydroxy-2-methylpropyl)-2-isopropyl-1H-indole-3,6-dicarboxamideHCID 69227964N3-(4-fluorobenzyl)-N6-(2-hydroxy-2-methylpropyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3,6-dicarboxamide

생성물 1

HCID 692279096-(5,5-Dimethyl-4,5-dihydrooxazol-2-yl)-N-(4-fluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

시약·촉매·용매 1

HCID 241Benzene용매

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온도
50 °C

실험 절차

To a solution of N3-(4-fluorobenzyl)-N6-(2-hydroxy-2-methylpropyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3,6-dicarboxamide (Compound 68, 23 mg, 0.043 mmol) in benzene (6 ml) at 25° C. was added P2O5 (120 mg, 0.86 mmol). The mixture was stirred at 50° C. for 4 h, quenched with 6N NaOH (1 ml), extracted several times with EtOAc, washed with H2O, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified by chromatography on silica gel (100% EtOAc) to yield the title compound as yellow oil.

후처리

  1. customquenched with 6N NaOH (1 ml)
  2. extractionextracted several times with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (100% EtOAc)

출처 및 근거

ORD 기록
ord-f16ce2aadef3440c99be1112c3cf515b
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524917B2

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