3-Methoxy-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid → (1R,2S)-1-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

HRID 1063262노트

반응식

HRID 1063262 반응식
[CH3:1][O:2][C:3]1[C:4](B(O)O)=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1.Br[C:17]1[N:18]=[C:19]([CH2:36][CH3:37])[C:20]([NH:25][C@@H:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][C@@H:27]2[OH:35])=[N:21][C:22]=1[CH2:23][CH3:24]>>[CH2:36]([C:19]1[C:20]([NH:25][C@@H:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][C@@H:27]2[OH:35])=[N:21][C:22]([CH2:23][CH3:24])=[C:17]([C:4]2[C:3]([O:2][CH3:1])=[CH:12][C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[N:18]=1)[CH3:37]

참가 물질

3

반응물 2

HCID 222788083-Methoxy-5,6,7,8-tetrahydronaphthalen-2-ylboronic acidHCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

생성물 1

HCID 23401193(1R,2S)-1-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol수율 67%

실험 절차

Following the general procedure of Example 1 Step 3 and making non-critical variations but substituting 6-methoxy-2,3-dihydro-1H-inden-5-ylboronic acid (Preparation 2) with 3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (Preparation 1), and substituting 5-bromo-3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine with (1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]indan-2-ol (303 mg, 0.84 mmol) and gave 550 mg of a crude orange oil. The crude was purified on a Biotage MPLC column (90 g column, 18% ethyl acetate in heptane) to give 249 mg (67%) of (1R,2S)-1-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol as a glassy paste. Rf 0.20 (25% ethyl acetate in heptane). OAMS supporting ions at: ESI+444.3. HRMS (ESI) calcd for C28H33N3O2+H1 444.2651, found 444.2635.

후처리

  1. customgave 550 mg of a crude orange oil
  2. customThe crude was purified on a Biotage MPLC column (90 g column, 18% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-8e4cd35945d0468cb14abd6654b56b2c
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964965B2

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