6-(Trifluoromethyl)nicotinoyl chloride → 6-(Trifluoromethyl)-N-(5-(2,3,4,5-tetrahydro-2,4-dioxo-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidin-6-yl)pyridin-2-yl)-N-(2-methoxyethyl)pyridin-3-carboxamide

HRID 2377726Notes

Reaction equation

HRID 2377726 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[NH:20][C:19]3[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH3:24])[C:16](=[O:25])[N:15]([CH2:26][CH2:27][CH3:28])[C:14]=3[CH:13]=2)=[CH:8][CH:7]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][N:32]=1>N1C=CC=CC=1>[F:40][C:30]([F:29])([F:41])[C:31]1[N:32]=[CH:33][C:34]([C:35]([N:5]([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[NH:20][C:19]4[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH3:24])[C:16](=[O:25])[N:15]([CH2:26][CH2:27][CH3:28])[C:14]=4[CH:13]=3)=[CH:10][N:11]=2)[CH2:4][CH2:3][O:2][CH3:1])=[O:36])=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 27775576-(Trifluoromethyl)nicotinoyl chlorideHCID 598566356-(6-(2-methoxyethylamino)pyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

Product 1

HCID 248162566-(Trifluoromethyl)-N-(5-(2,3,4,5-tetrahydro-2,4-dioxo-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidin-6-yl)pyridin-2-yl)-N-(2-methoxyethyl)pyridin-3-carboxamideYield 74.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9a (40 mg) was dissolved in pyridine (5 mL) at room temperature. 6-(Trifluoromethyl)nicotinoyl chloride (218 mg) was added. The mixture was stirred at room temperature for 24 h. After quenching with ice, the crude product was purified by column (26 g silica gel, RT Scientific) (CH2Cl2:MeOH=100:0 to 98:2) to give the 10a (43 mg).

Workup

  1. customAfter quenching with ice
  2. customthe crude product was purified by column (26 g silica gel, RT Scientific) (CH2Cl2:MeOH=100:0 to 98:2)

Sources & evidence

ORD record
ord-b3f8342cd18545ebb19af944d43ee3ee
Source dataset
uspto-grants-2008_12
Patent number
US07470697B2

Reaction notes

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