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Diisopropylethylamine → tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

HRID 1175911
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HRID 1175911 반응식
CCN(C(C)C)C(C)C.[CH3:10][O:11][CH2:12][C@@H:13]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1)[C:19]([OH:21])=O)[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:57][C:58]1[CH:62]=[CH:61][N:60]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[N:59]=1>CN(C=O)C.O>[CH3:14][C@H:13]([O:15][C:16]1[CH:17]=[C:18]([C:19]([NH:57][C:58]2[CH:62]=[CH:61][N:60]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[N:59]=2)=[O:21])[CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1)[CH2:12][O:11][CH3:10]
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51358380tert-Butyl 3-amino-1H-pyrazole-1-carboxylateHCID 59127150Benzoic acid, 3-[(1S)-2-methoxy-1-methylethoxy]-5-(phenylmethoxy)-

생성물 1

HCID 59127136
tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate
수율 74.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (28.5 mL, 164 mmol) was added to a suspension of 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[phenylmethyl]oxy}benzoic acid (20.7 g, 65.6 mmol), HATU (31.2 g, 82.0 mmol) and 1,1-dimethylethyl 3-amino-1H-pyrazole-1-carboxylate (15.0 g, 82.0 mmol) in DMF (30 mL) and the reaction mixture stirred for 16 hours at RT. Water (250 mL) was added and the reaction mixture extracted with diethyl ether (3×150 mL). The organic layer was washed with saturated brine solution and dried (MgSO4). The filtrate was concentrated in vacuo and the residue crystallised on standing. The crystals were washed with isohexane to give to give the desired material as yellow crystals (23.4 g; 73%). m/z 482 (M+H)+.

후처리

  1. extractionthe reaction mixture extracted with diethyl ether (3×150 mL)
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried (MgSO4)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue crystallised
  6. washThe crystals were washed with isohexane
  7. customto give

출처 및 근거

ORD 기록
ord-10f6a95c3dd04138a1a3b1080ed08101
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842694B2

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