Ammonia → (4-Aminomethyl-3-methyl-phenyl)-(1-benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-methanone

HRID 220987Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]([C:22]([C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([CH3:32])[CH:25]=3)=[O:23])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].N>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([C:22]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:33])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:17]=3[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=3)=[O:23])=[CH:25][C:26]=1[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(1-benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulene-6-carbonyl)-2-methyl-benzonitrile from Example E121.1 (830 mg, 1.9 mmol) in methanol (10 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (913 mg, 3.8 mmol). The mixture was stirred for 15 min then cooled down to 0° C. Sodium borohydride (726 mg, 19 mmol) was added portion-wise and the reaction mixture was stirred for 2 h at room temperature. 35% Ammonia (5 ml) was added dropwise and the mixture was stirred for 30 min then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloromethane) to yield the title compound (680 mg, 81%).

Workup

customat room temperature
stirringthe reaction mixture was stirred for 2 h at room temperature
stirringthe mixture was stirred for 30 min
concentrationthen concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloromethane)

Sources & evidence

ORD record: ord-fe29948b4deb4f44aee308502c54b122
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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