Triethylamine → Propane-1-sulfonic Acid 4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzylamide

HRID 220954Notes

Reaction equation

HRID 220954 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].Cl.[NH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([N:19]2[CH2:28][C:27]3[CH:26]=[N:25][N:24]([CH3:29])[C:23]=3[NH:22][C:21]3[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:20]2=3)=[O:18])=[CH:13][C:12]=1[F:35].C(N(CC)CC)C>ClCCl>[CH3:29][N:24]1[C:23]2[NH:22][C:21]3[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:20]=3[N:19]([C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH2:10][NH:9][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[C:12]([F:35])[CH:13]=3)=[O:18])[CH2:28][C:27]=2[CH:26]=[N:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 135736009(4-Aminomethyl-3-fluoro-phenyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Hydrochloride

Product 1

HCID 136128433Propane-1-sulfonic Acid 4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzylamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanesulfonyl chloride (0.016 ml, 0.14 mmol) was added to a solution of (4-aminomethyl-3-fluoro-phenyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride from Example E98.2 (50 mg, 0.12 mmol) in dichloromethane (2 ml) and triethylamine (0.038 ml, 0.27 mmol) at room temperature. The mixture was stirred for 1 h then concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane) to give a white solid identified as the title compound (30 mg, 51%).

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane)
  4. customto give a white solid

Sources & evidence

ORD record
ord-e5243d59fceb4f4e9ecbead221b5a7ac
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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