Diisopropylethylamine → (1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-yl)-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262218노트

반응식

HRID 1262218 반응식
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:35][S:36]([N:39]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([NH2:49])[CH:47]=2)[CH2:42][CH2:41][CH2:40]1)(=[O:38])=[O:37]>CN(C)C=O.CCOC(C)=O>[CH3:35][S:36]([N:39]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([NH:49][C:15]3[N:14]=[CH:13][C:12]4=[CH:11][CH:10]=[C:9]([C:6]5[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[N:17]4[N:16]=3)[CH:47]=2)[CH2:42][CH2:41][CH2:40]1)(=[O:38])=[O:37]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 91252911-(Methylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-amineHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

생성물 1

HCID 66712559(1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-yl)-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine수율 47.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (95.0 mg, 0.254 mmol) was dissolved in N,N-dimethylformamide (3.00 mL). N,N-diisopropylethylamine (133 uL, 0.761 mmol) was added followed by 1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (80.4 mg, 0.355 mmol) and the reaction was stirred overnight. The reaction was taken up in EtOAc (25 mL) and washed three times with water (25 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-70% EtOAc/hex as the eluting solvent to obtain the title compound as a yellow solid (54 mg, 47%). m.p.=202-203° C.; LCMS (m/e) 451 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.46 (s, 1H), 8.98 (s, 1H), 8.89 (s, 1H), 8.53 (dd, 1H, J=2.2 and 8.7 Hz), 7.81 (s, 1H), 7.53 (d, 1H, J=8.4 Hz), 7.19 (d, 1H, J=4.7 Hz), 7.10 (d, 1H, J=8.4 Hz), 7.02-6.93 (m, 2H), 3.93 (s, 3H), 3.74-3.68 (m, 2H), 2.99 (s, 3H), 2.79-2.72 (m, 2H), 1.97-1.88 (m, 2H).

후처리

  1. washwashed three times with water (25 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-5d2e900929284c809afcad778408a45d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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