1-Benzyloxymethyl-3-(3-carboxybenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 3-(3-Carboxybenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097406Notes

Reaction equation

HRID 2097406 reaction equation
C(OC[N:10]1[C:14]2[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=2[C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:29])=[O:28])[CH:22]=2)=[C:11]1[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[C:32]([O:40][CH:41]2[CH2:43][CH2:42]2)[CH:31]=1)C1C=CC=CC=1.C(OCN1C2C=NNC(=O)C=2C(CC2C=CC=CC=2F)=C1C1C=CC(OC(F)F)=C(OC2CC2)C=1)C1C=CC=CC=1>>[C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:12]1[C:13]2[C:18](=[O:19])[NH:17][N:16]=[CH:15][C:14]=2[NH:10][C:11]=1[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[C:32]([O:40][CH:41]2[CH2:43][CH2:42]2)[CH:31]=1)([OH:29])=[O:28]

Participants

3

Reactant 2

HCID 666027831-Benzyloxymethyl-3-(3-carboxybenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 66602968HCID 66602968, compound

Product 1

HCID 1358450433-(3-Carboxybenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 82%

Procedure

Reaction was carried out in the same manner as in Example 22-(b) except for using 1.05 g (1.79 mmol) of 1-benzyloxymethyl-3-(3-carboxybenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 27-(a) in place of 1-benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(2-fluorobenzyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one. After completion of the reaction, the reaction mixture was extracted with an alkaline aqueous solution with a pH 10, washed with diethyl ether, and after adjusting a pH of the aqueous layer to 2, the precipitated solid was collected by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 0.68 g of the title compound as a beige solid. (Yield: 82%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with an alkaline aqueous solution with a pH 10
  4. washwashed with diethyl ether
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe obtained solid was washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-bdead645505047be89d9935a47d7e2f0
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…