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

HRID 2097405Notes

Reaction equation

HRID 2097405 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]#[N:28])[CH:22]=2)=[C:11]1[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH:40]2[CH2:42][CH2:41]2)[CH:30]=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:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:37])[F:38])=[C:31]([O:39][CH:40]2[CH2:42][CH2:41]2)[CH:30]=1)#[N:28]

Participants

3

Reactant 2

HCID 666023911-Benzyloxymethyl-3-(3-cyanobenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 66602968HCID 66602968, compound

Product 1

HCID 1358450423-(3-Cyanobenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 20.8%

Procedure

Reaction was carried out in the same manner as in Example 22-(b) except for using 110 mg (0.193 mmol) of 1-benzyloxymethyl-3-(3-cyanobenzyl)-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 26-(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 suspension was filtered, the filtrate was concentrated under reduced pressure, methanol and 28% aqueous ammonia were added to the obtained solid, and the mixture was stirred for 1 hour. Then, the solution was concentrated under reduced pressure and the obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1→0:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 18 mg of the title compound as a white solid. (Yield: 20%)

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. filtrationthe reaction suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure, methanol and 28% aqueous ammonia
  5. additionwere added to the obtained solid
  6. concentrationThen, the solution was concentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a2fbbfcc9ca4803b0fef6032f02d8f3
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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