Hydrochloric Acid → N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzamide

HRID 889040Notes

Reaction equation

HRID 889040 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][O:15][C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)[CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:26][C:27]1[C:28](=[O:41])[N:29]([CH2:38][CH2:39][CH3:40])[C:30](=[O:37])[N:31]([CH2:34][CH2:35][CH3:36])[C:32]=1[NH2:33].CCN=C=NCCCN(C)C>CO>[NH2:33][C:32]1[N:31]([CH2:34][CH2:35][CH3:36])[C:30](=[O:37])[N:29]([CH2:38][CH2:39][CH3:40])[C:28](=[O:41])[C:27]=1[NH:26][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:16]([O:15][CH2:14][CH:10]2[CH2:11][C:12](=[O:13])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 104717594-[1-(4-Fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid

Product 1

HCID 57988770N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22.5 °C

Procedure

To a stirred solution of 4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid obtained in step 2 (0.140 g, 0.426 mmol) and HCl salt of 5,6-diamino-1,3-dipropyl-1H-pyrimidine-2,4-dione (0.112 g, 0.426 mmol) in MeOH (5 mL) was added EDCI (0.0136 g, 0.593 mmol). After stirring at 20-25° C. for 16 hours, the reaction mixture was quenched with water (5 mL). The solid obtained was filtered and washed with water to provide the crude product which was purified by column chromatography to afford N-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-[1-(4-fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzamide (0.205 g, 90%) as a white solid.

Workup

  1. customthe reaction mixture was quenched with water (5 mL)
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customto provide the crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-655f143abaf14331bb26229ea288fce4
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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