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

Reaction equation

HRID 1262148 reaction equation
[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]

Participants

3

Reactant 2

HCID 214367412-Methyl-1,2,3,4-tetrahydroisoquinolin-6-amineHCID 178449976HCID 178449976, compound

Product 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]-benzenesulfonamideYield 52.2%

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-28d0a3bbf9f44a5094cc2a01b694b6ac
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Linked notes

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