Dimethylamine → HCID 22032295, compound

HRID 1792584Notes

Reaction equation

HRID 1792584 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:45]=[CH:44][C:43]([CH2:46]O)=[CH:42][CH:41]=4)=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1.[CH3:48][NH:49][CH3:50]>[O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl>[CH3:48][N:49]([CH3:50])[CH2:46][C:43]1[CH:44]=[CH:45][C:40]([C:17]2[C:16]([C:13]3[CH:14]=[CH:15][C:10]4[N:11]([C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)=[CH:8][N:9]=4)[CH:12]=3)=[CH:20][N:19]([C:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:18]=2)=[CH:41][CH:42]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 22031800HCID 22031800, compound

Product 1

HCID 22032295HCID 22032295, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 296 mg {4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]phenyl}methanol (compound in Example 359), 844 mg manganese (IV) oxide and 20 mL chloroform was heated for 1 hour under reflux. The reaction solution was cooled to remove insolubles, and the filtrate was evaporated. 264 mg crude product of 4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]benzaldehyde was obtained as a pale brown amorphous. From 100 mg of this aldehyde derivative and 35 μL dimethylamine (50% aqueous solution), 81 mg of the title compound was obtained as a colorless amorphous under the same conditions as in Production Example 153.

Workup

  1. temperaturewas heated for 1 hour
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled
  4. customto remove insolubles
  5. customthe filtrate was evaporated
  6. custom264 mg crude product of 4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]benzaldehyde was obtained as a pale brown amorphous

Sources & evidence

ORD record
ord-6f2625f410d3427fb21178384597dbb8
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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