Triethylamine → HCID 178512291, compound

HRID 1157368Notes

Reaction equation

HRID 1157368 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.CS[C:17](=[N:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[NH:18][C:19]#[N:20].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:17]([NH:18][C:19]#[N:20])=[N:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155219651-Cyano-2-methyl-3-pyridin-4-yl-isothioureaHCID 231324436-(Pyridin-3-yloxy)-hexylamine

Product 1

HCID 178512291HCID 178512291, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 3-[6-amino-1-hexyl-oxy]-pyridine (150 mg), S-methyl-N-cyano-N′-4-pyridyl-isothiourea (123 mg), triethylamine (0.18 ml), 4-(N,N-dimethylamino)-pyridine (3.5 mg) and pyridine (5 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 (40:10:2.5) as eluent. The pure fractions were pooled and evaporated to give the title compound which crystallised from ethyl acetate.

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 (40:10:2.5) as eluent
  6. customevaporated

Sources & evidence

ORD record
ord-806d10be473144599b5d5751c7d4febb
Source dataset
uspto-grants-2010_10
Patent number
US07807682B2

Reaction notes

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