Trimethylsilyl isocyanate → 4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

HRID 2046923노트

반응식

HRID 2046923 반응식
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].C[Si]([N:31]=[C:32]=[O:33])(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][CH2:23][N:24]([C:32]([NH2:31])=[O:33])[CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

참가 물질

5

반응물 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 673640813-[1-(2,6-Dichloro-3-fluorophenyl)-ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 674021664-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)-ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (12.0 mg, 0.0307 mmol), trimethylsilyl isocyanate (8.32 μL, 0.0615 mmol), DIPEA (26.8 μL, 0.154 mmol) and DMF (0.5 mL) was stirred at rt for 20 min. The solution was concentrated in vacuo, redissolved in MeOH (0.5 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.87 (d, J=7.1 Hz, 3 H), 2.28-2.51 (m, 2 H), 3.60 (t, J=5.8 Hz, 2 H), 4.02 (q, J=2.5 Hz, 2 H), 5.26 (q, J=7.1 Hz, 1 H), 5.88-5.94 (m, 1 H), 7.18 (t, J=8.6 Hz, 1 H), 7.29 (d, J=2.0 Hz, 1 H), 7.32-7.55 (m, 2 H), 8.23 (br. s., 1 H). MS (ES+): m/z 433.02 (100) [MH+]. HPLC: tR=3.15 min (ZQ3, polar—5 min).

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH (0.5 mL)
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

출처 및 근거

ORD 기록
ord-988fe362d6c94d88ac9d8688a56c68b7
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592448B2

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