2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → tert-butyl 4-{(1S)-1-[({5-chloro-2-[3-(1,3-thiazol-2-yl)phenoxy]pyridin-3-yl}carbonyl)amino]ethyl}benzoate

HRID 1293184

반응식

HRID 1293184 반응식
Cl[C:2]1[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[C:32]1[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>C1(C)C=CC=CC=1>[Cl:26][C:5]1[CH:6]=[C:7]([C:8]([NH:10][C@H:11]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])[C:2]([O:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([C:28]3[S:27][CH:31]=[CH:30][N:29]=3)[CH:33]=2)=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 572848273-(1,3-Thiazol-2-yl)phenolHCID 57572256tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

생성물 1

HCID 69051089tert-butyl 4-{(1S)-1-[({5-chloro-2-[3-(1,3-thiazol-2-yl)phenoxy]pyridin-3-yl}carbonyl)amino]ethyl}benzoate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A mixture of tert-butyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate (step 1, 178 mg, 0.45 mmol), 3-(1,3-thiazol-2-yl)phenol (162 mg, 0.91 mmol) and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP, 217 μL, 0.75 mmol) in toluene (2 mL) was stirred at 110° C. for 5 h. After removal of solvent, the residue was eluted on silica gel short column (hexane/ethyl acetate (4/1)) to afford 259 mg (quant.) of the title compound as a white amorphous: 1H-NMR (CDCl3) δ 8.57 (1H, d, J=2.7 Hz), 8.15–8.11 (2H, m), 7.97–7.94 (2H, m), 7.90–7.83 (3H, m), 7.58–7.38 (3H, m), 7.34–7.20 (2H, m), 5.42–5.32 (1H, m), 1.61–1.57 (12H, m); MS (ESI) m/z 536 (M+H)+, 534 (M−H)−.

후처리

  1. customAfter removal of solvent
  2. washthe residue was eluted on silica gel short column (hexane/ethyl acetate (4/1))

출처 및 근거

ORD 기록
ord-7be45d7c55b3431bb1f035e9aef01061
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238714B2

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