1-Bromohexane → (6-Chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-(4-hexylaminomethyl-cyclohexyl)-methanone

HRID 220799Notes

Reaction equation

HRID 220799 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH: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]([Cl:34])[CH:32]=[CH:33][C:20]2=3)=[O:18])[CH2:13][CH2:12]1>CN(C=O)C.C(N(CC)CC)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:20]2[N:19]([C:17]([CH:14]3[CH2:13][CH2:12][CH:11]([CH2:10][NH:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:16][CH2:15]3)=[O:18])[CH2:28][C:27]3[CH:26]=[N:25][N:24]([CH3:29])[C:23]=3[NH:22][C:21]=2[CH:30]=1

Participants

5

Reactant 2

HCID 81011-BromohexaneHCID 135736042(4-Aminomethyl-cyclohexyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Hydrochloride

Product 1

HCID 136128444(6-Chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-(4-hexylaminomethyl-cyclohexyl)-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-bromohexane (0.83 mg, 0.005 mmol) in DMF (0.05 ml) was added to a solution of (4-Aminomethyl-cyclohexyl)-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride from Example E10.2 (2.05 mg, 0.005 mmol) in DMF (0.05 ml) and triethylamine (0.0021 ml). The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=458.4

Workup

  1. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-89bd6c7bb21e462dba7d84d46cdb46cb
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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