Diisopropylethylamine → 1,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate

HRID 527529노트

반응식

HRID 527529 반응식
[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2].[CH3:20][C:21]([O:24][C:25]([NH:27][C@H:28]([CH2:32][CH3:33])[C:29](O)=[O:30])=[O:26])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH:19][C:29]([C@H:28]([NH:27][C:25](=[O:26])[O:24][C:21]([CH3:23])([CH3:22])[CH3:20])[CH2:32][CH3:33])=[O:30])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679605196-[(3-Ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinamine2회

생성물 1

HCID 679668201,1-dimethylethyl {(1R)-1-[({6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinamine (Intermediate 33) was dissolved in DMF (0.5 mL) and added to a mixture of (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (7.7 mg, 0.038 mmol), DIPEA (0.008 mL, 0.047 mmol) and HATU (14.4 mg, 0.038 mmol) in 1 ml of DMF. The reaction mixture was then stirred at 50° C. for 2 hours. After the removal of DMF, water was added and the mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated. The residue was then charged on a silica gel column (Biotage SP1 system) and eluted with Cyhexane/EtOAc (from all 10/0 to 7/3, then 7/3) to afford the title compound (4.4 mg).

후처리

  1. customAfter the removal of DMF, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe gathered organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. additionThe residue was then charged on a silica gel column (Biotage SP1 system)
  8. washeluted with Cyhexane/EtOAc (from all 10/0 to 7/3

출처 및 근거

ORD 기록
ord-cfc3c38be1704db3950ed7ead1329242
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346790B2

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