Methylamine → 9-(4-Butyl-phenyl)-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methylamide

HRID 1690680Notes

Reaction equation

HRID 1690680 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:23]=[C:22]3[C:14]([C:15]4[CH2:16][CH2:17][C:18]5[CH:27]=[C:26]([C:28]([OH:30])=O)[CH:25]=[CH:24][C:19]=5[C:20]=4[NH:21]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:31][N:32](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.O1CCCC1>CN(C=O)C.C(OCC)(=O)C>[CH3:31][NH:32][C:28]([C:26]1[CH:25]=[CH:24][C:19]2[C:20]3[NH:21][C:22]4[C:14]([C:15]=3[CH2:16][CH2:17][C:18]=2[CH:27]=1)=[CH:13][CH:12]=[C:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=1)[CH:23]=4)=[O:30]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16048458HCID 16048458, compound

Product 1

HCID 160484599-(4-Butyl-phenyl)-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A sample of 9-(4-Butyl-phenyl)-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid (116.2 mg, 41 μmol) is dissolved in DMF (1 mL) and treated with HATU (16.3 mg, 41 μmol) and a solution of methylamine (2M) in tetrahydrofuran (0.1 mL, 100 μmol). After stirring overnight, the reaction is diluted with ethyl acetate and extracted with water twice. The organics are dried over MgSO4 and the solvent is removed. The resulting residue is purified by mass triggered HPLC to afford the title material as a white solid after lyophilisation. LC/MS calculated for [M+H]+ C28H29N2O: 409.5, found: 409.1

Workup

  1. extractionextracted with water twice
  2. dry with materialThe organics are dried over MgSO4
  3. customthe solvent is removed
  4. customThe resulting residue is purified by mass

Sources & evidence

ORD record
ord-cb58b27092524f0cbbd1edcbb110a3c1
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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