Ammonium Chloride → HCID 57555283, compound

HRID 220992Notes

Reaction equation

[CH3:1][C:2]1[CH:9]=[C:8]([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[S:18][C:17]([CH3:22])=[N:16][C:15]=3[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].[NH4+].[Cl-]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[S:18][C:17]([CH3:22])=[N:16][C:15]=3[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)=[O:11])=[CH:9][C:2]=1[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-methyl-4-(2-methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulene-6-carbonyl)-benzonitrile from Example E124.1 (190 mg, 0.53 mmol) in methanol (15 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (275 mg, 1.15 mmol). The mixture was stirred for 20 min then cooled down to 0° C. Sodium borohydride (200 mg, 5.3 mmol) was added portionwise and the mixture was stirred for 20 h at room temperature. Saturated NH4Cl (2 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 (100 mg, 52%).

Workup

customat room temperature
stirringthe mixture was stirred for 20 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-104970a79d8147908513d60e08a82468
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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