Triethylamine → HCID 178512288, compound

HRID 555329Notes

Reaction equation

HRID 555329 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:18].CS[C:21](=[N:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[NH:22][C:23]#[N:24].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:18]=[C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:21]([NH:22][C:23]#[N:24])=[N:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155219651-Cyano-2-methyl-3-pyridin-4-yl-isothioureaHCID 45117461HCID 45117461, compound

Product 1

HCID 178512288HCID 178512288, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(6-amino-1-hexyl)-1,2-dihydroquinoline-2-one (320 mg), S-methyl-N-cyano-N′-4-pyridyl-isothiourea (210 mg), triethylamine (0.31 ml), 4-(N,N-dimethylamino)-pyridine (7 mg) and pyridine (10 ml) was stirred overnight at 60° C. After cooling to room temperature the pyridine was removed by evaporation twice with toluene in vacuo and the residue was distributed between water and ethyl acetate. The organic phase was dried and evaporated to yield a crude product which was purified by chromatography on silica gel with ethyl acetate/methanol/aqueous ammonia (40:10:1.25) as eluent. The pure fractions were pooled, evaporated, triturated with ethyl acetate and dried in vacuo to give the title compound.

Workup

  1. customwas removed by evaporation twice with toluene in vacuo
  2. customThe organic phase was dried
  3. customevaporated
  4. customto yield a crude product which
  5. customwas purified by chromatography on silica gel with ethyl acetate/methanol/aqueous ammonia (40:10:1.25) as eluent
  6. customevaporated
  7. customtriturated with ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9208e559f07e4b7e954d9343a3ffba9f
Source dataset
uspto-grants-2011_11
Patent number
US08053446B2

Reaction notes

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