Ammonium Chloride → HCID 178432329, compound

HRID 220995Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]([C:15]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[CH:18]=3)=[O:16])[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:26])[NH:8][C:7]=3[C:6]=2[CH:27]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([C:15]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:26])[NH:8][C:7]=3[C:6]3[CH:27]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=3)=[O:16])=[CH:18][C:19]=1[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(9-chloro-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulene-6-carbonyl)-2-methyl-benzonitrile from E125.2 (80 mg, 0.2 mmol) in methanol (5 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (101 mg, 0.4 mmol). The mixture was cooled to 0° C. then sodium borohydride (80 mg, 2.1 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 30 min. then for 2 h at room temperature then saturated NH4Cl was added. The mixture was stirred for 10 min then the solid was filtered off through Celite® filter agent and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% di-chloromethane) to yield the title compound (24 mg, 30%).

Workup

waitfor 2 h at room temperature
stirringThe mixture was stirred for 10 min
filtrationthe solid was filtered off through Celite®
filtrationfilter agent
concentrationthe filtrate concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% di-chloromethane)

Sources & evidence

ORD record: ord-c3ccfeb4619141969a95485a6e0f1e4c
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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