Acetic Acid → HCID 89925772, compound

HRID 2280210Notes

Reaction equation

HRID 2280210 reaction equation
[NH2:1][C:2]1[S:14][C:13]2[CH2:12][C@@H:11]3[C@H:6]([CH2:7][C@@H:8]([C:16]([N:18]([CH2:27][CH2:28][CH3:29])[C:19]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:20])=[O:17])[CH2:9][N:10]3[CH3:15])[CH2:5][C:4]=2[C:3]=1[C:30]#[N:31].[C:32](O)(=[O:34])[CH3:33]>>[C:30]([C:3]1[C:4]2[CH2:5][C@@H:6]3[C@@H:11]([CH2:12][C:13]=2[S:14][C:2]=1[NH:1][C:32](=[O:34])[CH3:33])[N:10]([CH3:15])[CH2:9][C@H:8]([C:16]([N:18]([C:19](=[O:20])[NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:27][CH2:28][CH3:29])=[O:17])[CH2:7]3)#[N:31]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 665485291399442-97-7

Product 1

HCID 89925772HCID 89925772, compound

Conditions

Temperature
135 °C

Procedure

To 1-{[(4aR*,6R*,8aR*)-2-amino-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H, 8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[2-(dimethylamino)ethyl]-1-propylurea (example 1-15) (100 mg) was added acetic acid (2 mL) and the mixture was heated at 135° C. and refluxed for 12 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and a saturated aqueous solution of sodium bicarbonate. After the separated organic layer was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution) to give the title compound (26 mg). The structure was illustrated in Table 11.

Workup

  1. temperaturerefluxed for 12 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue were added ethyl acetate
  5. dry with materialAfter the separated organic layer was dried over anhydrous sodium sulfate, it
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-f15f7a27c26e4f7589d1f815c9e2a061
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

Loading…