1-Benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(6-methoxy-2-pyridylmethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(6-methoxy-2-pyridylmethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097407Notes

Reaction equation

HRID 2097407 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]([O:27][CH3:28])[N: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>>[CH:40]1([O:39][C:31]2[CH:30]=[C:29]([C:11]3[NH:10][C:14]4[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=4[C:12]=3[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[N:22]=3)[CH:34]=[CH:33][C:32]=2[O:35][CH:36]([F:38])[F:37])[CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 666024621-Benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(6-methoxy-2-pyridylmethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-oneHCID 66602968HCID 66602968, compound

Product 1

HCID 1358450442-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(6-methoxy-2-pyridylmethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 22%

Procedure

Reaction was carried out in the same manner as in Example 22-(b) except for using 227 mg (0.396 mmol) of 1-benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(6-methoxy-2-pyridylmethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one obtained in Example 28-(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; chloroform:ethyl acetate=1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 39 mg of the title compound as a white solid. (Yield: 22%)

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-c4225f3915f144a992b474f102606680
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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