Toluene → 4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide

HRID 16856Notes

Reaction equation

HRID 16856 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][N:8]([C:10]3[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=3)[CH2:9][CH:2]12.Cl.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][O:32][C:33]2[CH:34]=[C:35]([NH2:38])[NH:36][N:37]=2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1.C[Al](C)C.C1(C)C=CC=CC=1>>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][N:8]([C:10]3[CH:11]=[CH:12][C:13]([C:14]([NH:38][C:35]4[NH:36][N:37]=[C:33]([O:32][CH2:31][C:25]5[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=[C:23]([O:22][CH3:21])[CH:24]=5)[CH:34]=4)=[O:16])=[CH:18][CH:19]=3)[CH2:9][CH:2]12

Participants

5

Reactant 4

HCID 1140TolueneHCID 16682925TrimethylaluminumHCID 574403805-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine hydrochlorideHCID 66589763Methyl 4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)benzoate

Product 1

HCID 665897144-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamideYield 30.5%

Procedure

4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide was prepared following the procedure as for Example 115, but starting from methyl 4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)benzoate (0.221 g, 0.85 mmol) and 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine HCl (0.243 g, 0.85 mmol) and 2M trimethylaluminium in toluene (1.06 ml, 2.13 mmol). The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.124 g, 30.5%) as a white solid.

Workup

  1. custom4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide was prepared
  2. customThe crude product was purified by preparative HPLC
  3. additionFractions containing the desired compound
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-9566cd0f28204d5ab41afdff0d98906b
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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