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

HRID 2406110Notes

Reaction equation

HRID 2406110 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-974db1f3fe99406dbc8d6292d9c65b1e
Source dataset
uspto-grants-2014_08
Patent number
US08809339B2

Reaction notes

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