Isopropylamine → N-Ethyl-2-[4-(2-isopropylamino-pyrimidin-5-ylethynyl)-phenyl]-propionamide

HRID 330840Notes

Reaction equation

HRID 330840 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[N:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:26])[C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH2:24]([NH:23][C:21](=[O:22])[CH:20]([C:17]1[CH:16]=[CH:15][C:14]([C:13]#[C:12][C:9]2[CH:8]=[N:7][C:6]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:11][CH:10]=2)=[CH:19][CH:18]=1)[CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 866695682-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide

Product 1

HCID 56929772N-Ethyl-2-[4-(2-isopropylamino-pyrimidin-5-ylethynyl)-phenyl]-propionamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 9.3 mg (0.16 mmol) isopropylamine in 0.5 mL DMSO are added 31 mg (0.10 mmol) 2-[4-(2-chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide (XVIII.1) in 1 mL DMSO, followed by 254 (16 mmol) DIPEA. The mixture is stirred at rt for 12 h. After that time, the mixture is directly purified by HPLC (preparative column: Sunfire; eluent A: water+0.1% TFA, eluent B: MeOH) to yield the desired product.

Workup

  1. customAfter that time, the mixture is directly purified by HPLC (preparative column: Sunfire; eluent A: water+0.1% TFA, eluent B: MeOH)

Sources & evidence

ORD record
ord-d0740ad3470c4c5ba6fcaabc22edd26f
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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