Sodium Hydroxide → HCID 70133158, compound

HRID 1107987Notes

Reaction equation

HRID 1107987 reaction equation
Cl.CN(C)CCCN=C=NCC.O[N:14]1[C:18]2N=CC=CC=2N=[N:15]1.CC1C=C(C)C2C(=C([O:35][CH2:36][C:37]3[C:38](Cl)=[C:39](S(N4CCC[C@H]4C(NCCN)=O)(=O)=O)[CH:40]=[CH:41][C:42]=3[Cl:43])C=CC=2)N=1.[OH-:59].[Na+]>CN(C)C=O.O>[ClH:43].[NH2:15][N:14]=[CH:18][C:40]1[CH:41]=[CH:42][C:37]([C:36]([OH:35])=[O:59])=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11827764HCID 11827764, compound

Product 1

HCID 70133158HCID 70133158, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 0.15 g (7.25.10-4 mol) of 4-(aminoiminomethyl)benzoic acid hydrochloride in 10 ml of dimethylformamide (DMF) is prepared and 0.15 g (7.98.10-4 mol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 0.11 g (7.25.10-4 mol) of 1-hydroxy-7-azabenzotriazole (HOAT) are added. The resulting mixture is stirred for 30 minutes at room temperature (about 20° C.) and a solution of 0.4 g (7.25.10-4 mol) of 1-[[3-[(2,4-dimethylquinolin-8-yl)oxymethyl]-2,4-dichlorophenyl]sulfonyl]-N-[2-aminoethyl]-2(S)-pyrrolidine-carboxamide in 10 ml of DMF is then added dropwise. The reaction medium is stirred for 5 hours at room temperature and then poured into iced water. 1 N sodium hydroxide solution is then added slowly until the pH is 8, after which the mixture is extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The crude product is purified by chromatography on NH2 -grafted silica gel (LICHROPREP® NH2) using a dichloromethane/methanol mixture (95/5; v/v) as the eluent to give 0.2 g of the expected product (yield=40%). The product is used directly to obtain the salt.

Workup

  1. stirringThe reaction medium is stirred for 5 hours at room temperature
  2. extractionafter which the mixture is extracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by chromatography on NH2 -grafted silica gel (LICHROPREP® NH2)

Sources & evidence

ORD record
ord-6b2e31c3dba940beb16dfca62c13ffbe
Source dataset
uspto-grants-2000_05
Patent number
US06063791

Reaction notes

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