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Triphenylphosphine → 4-((4-(Difluoromethyl)-1,3-thiazol-2-yl)methoxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203111
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HRID 2203111 반응식
[F:1][CH:2]([F:10])[C:3]1[N:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1.[CH2:11]([C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[C:20]([N:23]3[CH:28]=[CH:27][C:26](O)=[CH:25][C:24]3=[O:30])[CH:21]=[CH:22][C:15]=2[N:14]=1)[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>O.C1COCC1>[F:1][CH:2]([F:10])[C:3]1[N:4]=[C:5]([CH2:8][O:9][C:26]2[CH:27]=[CH:28][N:23]([C:20]3[CH:21]=[CH:22][C:15]4[N:14]=[C:13]([CH2:11][CH3:12])[N:17]([CH3:18])[C:16]=4[CH:19]=3)[C:24](=[O:30])[CH:25]=2)[S:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 680963792-Thiazolemethanol, 4-(difluoromethyl)-HCID 896909981-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 897026674-((4-(Difluoromethyl)-1,3-thiazol-2-yl)methoxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
수율 13.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (4-(difluoromethyl)-1,3-thiazol-2-yl)methanol (61.3 mg), 1-(2-ethyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (50 mg), triphenylphosphine (146 mg), bis(2-methoxyethyl) azodicarboxylate (130 mg) and THF (3 ml) was stirred at room temperature for 3 h. The mixture was diluted with water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (10.1 mg) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-9ee8129c1882422a8895680434487701
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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