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 1262218ノート

反応式

HRID 1262218 の反応式
[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]

参加物

6

反応物 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

生成物 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]-amine収率 47.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5d2e900929284c809afcad778408a45d
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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