Dimethylcarbamoyl Chloride → HCID 59161235, compound

HRID 545550Notes

Reaction equation

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

Participants

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride

HCID 57431673HCID 57431673, compound

Product 1

HCID 59161235HCID 59161235, compoundYield 69%

Procedure

Prepare the title compound by essentially following the procedures as described in Example 162, using 6-amino-9-(3-fluoro-benzyl)-6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile hydrochloride (Preparation 54) and dimethylcarbamyl chloride. Purify by silica gel chromatography (30-70% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes) to give the title compound in 69% yield as a white solid. MS (ES): m/z 391 (M+1), 389 (M−1); HPLC (Method B): Rt=4.11 min (99%).

Workup

customPurify by silica gel chromatography (30-70% (4% (2M NH3/MeOH)/CH2Cl2)/hexanes)

Sources & evidence

ORD record: ord-7a3e312cb06e432c9768c8cfde963997
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935722B2

Reaction notes

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