Triethylamine → HCID 68540408, compound

HRID 2243490Notes

Reaction equation

HRID 2243490 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11]([C:13]1[S:27][C:16]2[C:17]3[CH:18]=[CH:19][C:20]([C:24]([OH:26])=O)=[CH:21][C:22]=3[S:23][C:15]=2[C:14]=1[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:9][O:10][C:11]([C:13]1[S:27][C:16]2[C:17]3[CH:18]=[CH:19][C:20]([C:24](=[O:26])[NH:8][CH2:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:21][C:22]=3[S:23][C:15]=2[C:14]=1[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68540407HCID 68540407, compound

Product 1

HCID 68540408HCID 68540408, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyclohexanemethyamine (29 μl, 0.22 mmol) was added to a mixture of 1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2,6-dicarboxylic acid 2-methyl ester (42 mg, 0.11 mmol), HATU (49 mg, 0.13 mmol), and Et3N (50 1) in DMF (0.5 ml). The mixture was stirred for 2 days. Addition of EtOAc, washing with water, drying organic layers over MgSO4, filtration, and reoval of solvent in vacuo left crude material. Purification by column chromatography yielded 30 mg (58%) of 6-(cyclohexylmethylcarbamoyl)-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester.

Workup

  1. washwashing with water
  2. customdrying organic layers
  3. filtrationover MgSO4, filtration, and reoval of solvent in vacuo
  4. waitleft crude material
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-8ffddf6d87ff4448afad54f54a24da9e
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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