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Morpholine → 1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid

HRID 449160
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HRID 449160 반응식
C([O:4][C:5]([C:7]1([NH:10][C:11]([C:13]2[N:17]3[C@@:18]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=4)([CH3:31])[C:19](=[O:30])[N:20]([C:21]4[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[C:23]([Cl:29])[CH:22]=4)[C:16]3=[N:15][CH:14]=2)=[O:12])[CH2:9][CH2:8]1)=[O:6])C=C.N1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C@@:18]2([CH3:31])[N:17]3[C:13]([C:11]([NH:10][C:7]4([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]4)=[O:12])=[CH:14][N:15]=[C:16]3[N:20]([C:21]3[CH:22]=[C:23]([Cl:29])[C:24]([F:28])=[C:25]([Cl:27])[CH:26]=3)[C:19]2=[O:30])=[CH:34][CH:35]=1)#[N:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 8083MorpholineHCID 680892731-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazol[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid allyl ester

생성물 1

HCID 673908991-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

The ester obtained (12.6 g, 22 mmol) was combined with THF (100 mL). Morpholine (18.6 mL, 210 mmol) and Pd(PPh3)4 (500 mg, 0.40 mmol) were added and the reaction was allowed to stir at room temperature for 16 h. The solution was filtered through diatomaceous earth and then concentrated. The residue was diluted with ethyl acetate (150 mL) washed with water (2×50 mL), 1M HCl (2×50 mL), brine (1×50 mL) and then dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica-gel) using 10-100% ethyl acetate in hexanes to provide 10.4 g of the title compound.

후처리

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate (150 mL)
  4. washwashed with water (2×50 mL), 1M HCl (2×50 mL), brine (1×50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica-gel)

출처 및 근거

ORD 기록
ord-ec8dd4de326f41e69f0efa12e82ac254
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481750B2

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