Phenyl formate → (S)-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-3-(isopropylamino)-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carbaldehyde

HRID 713354

반응식

HRID 713354 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([F:30])[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[C:18]3[CH2:29][CH2:28][NH:27][CH2:26][C:19]3=[N:20][C:21]=2[NH:22][CH:23]([CH3:25])[CH3:24])[CH2:12][CH2:11]1.[CH:31](OC1C=CC=CC=1)=[O:32]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([F:30])[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[C:18]3[CH2:29][CH2:28][N:27]([CH:31]=[O:32])[CH2:26][C:19]3=[N:20][C:21]=2[NH:22][CH:23]([CH3:25])[CH3:24])[CH2:12][CH2:11]1

참가 물질

4

반응물 2

HCID 74626Phenyl formateHCID 118159152HCID 118159152, 화합물

생성물 1

HCID 118159387(S)-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-3-(isopropylamino)-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A solution of (S)-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine (30.5 mg, 0.073 mmol) in THF (364 μL) at room temperature was treated with phenyl formate (140 μL, 1.09 mmol). The reaction mixture was stirred at 60° C. for 1 h. The reaction was purified by HPLC Method B using a 50% to 80% ACN gradient to give the title compound, as a TFA salt, as a pale yellow solid (9.4 mg, 23%). 1H NMR (500 MHz, methanol-d4, mixture of rotamers) δ ppm 1.29 (m, 6H), 1.45 (d, J=12.7 Hz, 1H), 1.66 (m, 2H), 2.00 (m, 1H), 2.10 (m, 1H), 2.77 (m, 4H), 3.49 (m, 2H), 3.76 (t, J=5.9 Hz, 1.4H), 3.82 (t, J=6.1 Hz, 0.6H), 4.12 (m, 1H), 4.48 (s, 0.6H), 4.52 (s, 1.4H), 5.53 (m, 1H), 7.02 (m, 2H), 7.50 (td, J=8.3, 6.3 Hz, 1H), 8.18 (s, 0.7H), 8.24 (s, 0.3H); ESI-MS m/z [M+H]+ 447.90.

후처리

  1. customThe reaction was purified by HPLC Method B

출처 및 근거

ORD 기록
ord-18a6393dd64143529a69044fe87e7af2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181249B2

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