Tetrahydrofuran → HCID 22100435, compound

HRID 1457764Notes

Reaction equation

HRID 1457764 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=2)[O:4][CH2:3]1.[CH2:14]([C:16]1[C:17](=[O:22])[NH:18][CH2:19][C:20]=1[CH3:21])[CH3:15].C1C[O:26][CH2:25]C1>>[CH2:14]([C:16]1[C:17](=[O:22])[N:18]([C:25]([NH:1][CH:2]2[CH2:11][C:10]3[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=3)[O:4][CH2:3]2)=[O:26])[CH2:19][C:20]=1[CH3:21])[CH3:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8541463-Ethyl-4-methyl-3-pyrrolin-2-oneHCID 30416017-methoxychroman-3-amine

Product 1

HCID 22100435HCID 22100435, compound

Procedure

8.43 g (52 mmol) of N,N'-carbonyldiimidazole were added to a solution of 8.2 g (46 mmol) of 3-amino-7-methoxychroman in 60 ml of THF. During this operation, the solution became warm. After the solution had been stirred at room temperature for one hour, it was evaporated in vacuo. The residue was melted together with 6.51 g (52 mmol) of 3-ethyl-4-methyl-3-pyrrolin-2-one at 160°-170° C. for 1.5 to 2 hours and the mixture was then chromatographed over silica gel using the eluting agent ethyl acetate/petroleum ether 3:1. The main fraction was evaporated and the residue was recrystallized from methanol. 3-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-7-methoxychroman of melting point 118°-119° C. was obtained. This product was introduced by the customary procedure into chlorosulfonic acid which had been cooled to -15° C. The mixture was allowed to come to room temperature and was subsequently stirred for 1 hour. After customary work-up, the sulfochloride was converted into the sulfonamide as described in Example 1. 3-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-6-sulfamoyl-7-methoxychroman had a melting point of 225°-227° C.

Workup

  1. temperatureDuring this operation, the solution became warm
  2. customit was evaporated in vacuo
  3. customthe mixture was then chromatographed over silica gel using the eluting agent ethyl acetate/petroleum ether 3:1
  4. customThe main fraction was evaporated
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-167b86611f144b588fb57f31ff9ba68d
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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