Diisopropylethylamine → 2-(3-(chloromethyl)benzamido)-N-(5-phenylpyrimidin-2-yl)-5-(piperidin-1-yl)benzamide

HRID 926801Notes

Reaction equation

HRID 926801 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:3]=1[C:4]([NH:6][C:7]1C=NC(C2C=CC=CC=2)=NC=1)=[O:5].C(N([CH:35]([CH3:37])[CH3:36])CC)(C)C.[Cl:38][CH2:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=1)[C:43](Cl)=[O:44]>C1COCC1.C(Cl)Cl>[Cl:38][CH2:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=1)[C:43]([NH:1][C:2]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[N:6]=[CH:4][C:3]([C:36]2[CH:35]=[CH:37][CH:21]=[CH:20][CH:19]=2)=[CH:2][N:1]=1)=[O:5])=[O:44]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 665870272-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide

Product 1

HCID 665881802-(3-(chloromethyl)benzamido)-N-(5-phenylpyrimidin-2-yl)-5-(piperidin-1-yl)benzamide

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a 0° C. solution of 100 mg of 2-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide 2d, and 138 mg of diisopropylethylamine in 2 mL of 1:1 THF/DCM was added dropwise 46 mg of 3-(chloromethyl)benzoyl chloride. The mixture was stirred overnight at room temperature and the solvent was evaporated. All of this material was used in the next step without further characterization.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9b7af72ccab74b4f9d28511fb077dff7
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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