Diisopropylethylamine → HCID 86654738, 화합물

HRID 516090

반응식

HRID 516090 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])[CH2:10][C:6]=2[C:5]([F:23])=[C:4](Cl)[N:3]=1.[O:25]1[CH2:30][CH2:29][C@@H:28]([NH2:31])[C@@H:27]([NH2:32])[CH2:26]1.CCN(C(C)C)C(C)C>C(#N)C>[NH2:32][C@@H:27]1[C@H:28]([NH:31][C:4]2[N:3]=[C:2]([Cl:1])[C:7]3[C:8](=[O:22])[N:9]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=4[O:20][CH3:21])[CH2:10][C:6]=3[C:5]=2[F:23])[CH2:29][CH2:30][O:25][CH2:26]1

참가 물질

5

반응물 3

HCID 81531Diisopropylethylamine2회HCID 583175754,6-dichloro-2-[(2,4-dimethoxyphenyl)methyl]-7-fluoro-1H,2H,3H-pyrrolo[3,4-c]pyridin-3-oneHCID 58648761HCID 58648761, 화합물2회

생성물 1

HCID 86654738HCID 86654738, 화합물수율 9.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

A mixture of 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2 H)-one (2.5 g, 6.74 mmol), (3R,4R)-tetrahydro-2H-pyran-3,4-diamine (0.711 g, 6.12 mmol), and DIPEA (5.35 mL, 30.6 mmol) in ACN (30 mL) was stirred at 85° C. for 3 d in a sealed tube. Additional (3R,4R)-tetrahydro-2H-pyran-3,4-diamine (0.356 g, 3.06 mmol) and DIPEA (2.14 mL, 12.2 mmol) were added and the mixture was heated at 100° C. overnight. The mixture was concentrated and purified via preparative HPLC. The fractions corresponding to the desired regioisomer were collected to give the title compound (265 mg, 9.60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.65 (m, 1 H), 1.80-1.82 (s, 1 H), 3.40 (td, J=11.47, 2.44 Hz, 1 H), 3.53 (dd, J=11.23, 1.95 Hz, 1 H), 3.67 (dd, J=11.47, 2.20 Hz, 1 H), 3.71-3.73 (m, 1 H), 3.75 (s, 3 H), 3.77-3.79 (m, 1 H), 3.81 (s, 3 H), 4.09-4.11 (m, 1 H), 4.33 (s, 2 H), 4.50 (s, 2 H), 6.48 (dd, J=8.30, 2.44 Hz, 1 H), 6.58 (d, J=2.44, 1 H), 6.90 (br s, 1 H), 7.06 (d, J=8.30 Hz, 1 H). [M+H] calc'd for C21H24ClFN4O4, 451; found, 451.

후처리

  1. temperaturethe mixture was heated at 100° C. overnight
  2. concentrationThe mixture was concentrated
  3. custompurified via preparative HPLC
  4. customThe fractions corresponding to the desired regioisomer were collected

출처 및 근거

ORD 기록
ord-cba1bbe98218499a9518bd535379fc56
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108970B2

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