Methanesulfonyl chloride → N-[4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-methanesulfonamide

HRID 220804Notes

Reaction equation

HRID 220804 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:25][C:24]3[CH:23]=[N:22][N:21]([CH3:26])[C:20]=3[NH:19][C:18]3[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:17]2=3)=[O:15])[CH2:10][CH2:9]1>ClCCl.C(N(CC)CC)C>[CH3:26][N:21]1[C:20]2[NH:19][C:18]3[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:17]=3[N:16]([C:14]([CH:11]3[CH2:12][CH2:13][CH:8]([CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:9][CH2:10]3)=[O:15])[CH2:25][C:24]=2[CH:23]=[N:22]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 136128398(4-aminomethyl-cyclohexyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

Product 1

HCID 136128403N-[4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of methanesulfonyl chloride (0.57 mg, 0.005 mmol) in dichloromethane (0.05 ml) was added to a solution of (4-aminomethyl-cyclohexyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone (Compound number 149) (1.95 mg, 0.005 mmol) in dichloromethane (0.05 ml) and triethylamine (0.0035 ml). The mixture was stirred at room temperature for 1 h then solvents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=432.1

Workup

  1. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-1dd0d086409f4f7fa8118d931b070b9e
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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