1-(Cyclopropylmethyl)pyrrolidine-2-methylamine → N-(1-cyclopropylmethyl-2-pyrrolidylmethyl)-2-methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzamide

HRID 652758Notes

Reaction equation

HRID 652758 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH:6]2[CH2:10][NH2:11])[CH2:3][CH2:2]1.[CH3:12][O:13][C:14]1[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][C:20]([S:26](=[O:29])(=[O:28])[NH2:27])=[C:19]([CH3:30])[C:15]=1[C:16](Cl)=[O:17]>CC(CC)=O>[CH:1]1([CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH:6]2[CH2:10][NH:11][C:16](=[O:17])[C:15]2[C:19]([CH3:30])=[C:20]([S:26](=[O:29])(=[O:28])[NH2:27])[CH:21]=[C:22]([CH:23]([CH3:25])[CH3:24])[C:14]=2[O:13][CH3:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 30182741-(Cyclopropylmethyl)pyrrolidine-2-methylamineHCID 201968202-Methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoyl chloride

Product 1

HCID 54114554N-(1-cyclopropylmethyl-2-pyrrolidylmethyl)-2-methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzamideYield 24%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
10 °C

Procedure

4.3 g of 1-cyclopropylmethyl-2-aminomethylpyrrolidine (0.028 mole) and 40 ml of methylethyl ketone are placed in 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The mixture is cooled to about 10° C. and a solution of 7.6 g of 2-methoxy-3-isopropyl-5-sulphamoyl-6-methyl benzoyl chloride (0.025 mole) in 50 ml of methyl-ethyl-ketone is poured in drop by drop. The mixture is reacted for 1 hour at room temperature then evaporated dry under vacuum, and the residue is dissolved in 100 ml of water and 10 ml of hydrochloric acid (density 1.18). The solution is sucked up under vacuum to eliminate the last traces of solvent, an insoluble component is filtered off and the filtrate is made alkaline with 15 ml of ammonia (density=0.91). The precipitate formed is filtered, washed with water and re-crystallised moist in 50 ml of ethyl acetate. 2.5 g (24%) of product is obtained, melting at about 125° C.

Workup

  1. customfitted with an agitator
  2. customThe mixture is reacted for 1 hour at room temperature
  3. customthen evaporated
  4. customdry under vacuum
  5. dissolutionthe residue is dissolved in 100 ml of water
  6. filtrationan insoluble component is filtered off
  7. customThe precipitate formed
  8. filtrationis filtered
  9. washwashed with water
  10. customre-crystallised moist in 50 ml of ethyl acetate

Sources & evidence

ORD record
ord-74544cdc71c64ca7bc97c19755769a8d
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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