PD-173074 → HCID 86713615, compound

HRID 2274243Notes

Reaction equation

HRID 2274243 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[C:10]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=2)=[CH:11][C:12]2[CH:17]=[N:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[N:14][C:13]=2[N:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39](Cl)(=[O:42])[CH:40]=[CH2:41].C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([NH:5][C:6](=[O:7])[NH:8][C:9]1[C:10]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=2)=[CH:11][C:12]2[CH:17]=[N:16][C:15]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])[C:39](=[O:42])[CH:40]=[CH2:41])=[N:14][C:13]=2[N:28]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1401PD-1730742×HCID 13140Acryloyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 86713615HCID 86713615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material 1-(tert-butyl)-3-(2-((4-(diethylamino)butyl)amino)-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl)urea (PD173074) can be purchased from, e.g., SelleckChem.com. In a dried vessel, acryloyl chloride (2 equiv.) and diisopropylethylamine (4.3 equiv.) are added to a solution of 1-(tert-butyl)-3-(2-((4-(diethylamino)butyl)amino)-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl)urea (1 equiv.) in anhydrous dichloromethane at 0° C. After stirring at room temperature for 2 hours, the reaction mixture is concentrated, diluted with DMSO and purified by reverse phase HPLC (5-95% water/acetonitrile). After concentrating the fractions, the product N-(7-(3-(tert-butyl)ureido)-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-N-(4-(diethylamino)butyl)acrylamide is obtained as a pale yellow foam. LCMS (M+1)=578.2.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. additiondiluted with DMSO
  3. custompurified by reverse phase HPLC (5-95% water/acetonitrile)
  4. concentrationAfter concentrating the fractions

Sources & evidence

ORD record
ord-f3c0336b69c0418f99ef2d4ebbc3c4f1
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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