Dimethylcarbamoyl Chloride → (+/-)-3-[7-Cyano-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-1,1-dimethyl-urea

HRID 2427276Notes

Reaction equation

HRID 2427276 reaction equation
[NH2:1][CH:2]1[CH2:23][C:5]2[N:6]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=3)[C:7]3[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.C(N(C(C)C)CC)(C)C.[CH3:33][N:34]([CH3:38])[C:35](Cl)=[O:36]>ClCCl>[C:13]([C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=3)[C:5]3[CH2:23][CH:2]([NH:1][C:35](=[O:36])[N:34]([CH3:38])[CH3:33])[CH2:3][C:4]=3[C:12]=2[CH:11]=1)#[N:14]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 59242745(+/-)-2-Amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile

Product 1

HCID 59242739(+/-)-3-[7-Cyano-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-1,1-dimethyl-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-2-amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (70 mg, 0.23 mmol) and diisopropylethylamine (0.35 mmol, 61 μL) in dichloromethane (1 mL) add N,N-dimethylcarbamoyl chloride (0.35 mmol, 32 μL) and stir at room temperature overnight. Load the solution on silica gel and purify by column chromatography (0-100% ethyl acetate/dichloromethane) to obtain the title compound. LCMS 378.1 (M+1).

Workup

  1. customLoad the solution on silica gel and purify by column chromatography (0-100% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-150e4166230c491d9661cbc7fde94132
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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