2-Methyl-1,2,3,4-tetrahydroisoquinolin-6-amine → N-tert-Butyl-3-[2-(2-methyl-1,2,3,4-tetrahydro-iso quinolin-6-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide

HRID 1262148

反応式

HRID 1262148 の反応式
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([NH2:36])[CH:32]=2)[CH2:27]1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:36][C:31]4[CH:32]=[C:33]5[C:28](=[CH:29][CH:30]=4)[CH2:27][N:26]([CH3:25])[CH2:35][CH2:34]5)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

3

反応物 2

HCID 214367412-Methyl-1,2,3,4-tetrahydroisoquinolin-6-amineHCID 178449976HCID 178449976、化合物

生成物 1

HCID 66712000N-tert-Butyl-3-[2-(2-methyl-1,2,3,4-tetrahydro-iso quinolin-6-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide収率 52.2%

実験手順

N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (0.109 g, 0.316 mmol) and 2-Methyl-1,2,3,4-tetrahydro-isoquinolin-6-ylamine (0.064 g, 0.39 mmol) were reacted in an analogous manner to Example 908D at rt for 16 h. The reaction mixture was concentrated, taken up in EtoAc, and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting solid was purified by ISCO silica gel chromatography (0-10% MeOH in CH2Cl2) to afford title compound (81 mg, 52%). HPLC purity=96%, rt=2.654, LCMS=491.0 (M+H) 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.48 (s, 1H), 9.04 (s, 1H), 8.50 (d, J=7.9 Hz, 1H), 8.39 (s, 1H), 7.84 (d, J+7.4 Hz, 1H), 7.73 (dd, J=7.9 Hz, 7.9 Hz, 1H), 7.61 (s, 1H), 7.58 (s, 1H0, 7.48 (dd, J=8.3 Hz, 1.67 Hz, 1H), 7.18 (d, J=4.7 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 7.00 (d, J=4.8 Hz, 1H), 3.67-3.61 (m, 2H), 2.85 (s, 3H), 2.80-2.70 (m, 2H), 2.48-2.42 (m, 2H), 1.11 (s, 9H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was purified by ISCO silica gel chromatography (0-10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-28d0a3bbf9f44a5094cc2a01b694b6ac
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

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