Dichloromethane → N-(3-(2-(4-(1-(2-fluoroethyl)azetidin-3-ylamino)-2-methoxyphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl) acrylamide

HRID 2359366Notes

Reaction equation

HRID 2359366 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[C:7]2[CH:31]=[CH:30][NH:29][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH:20]3[CH2:23][N:22]([CH2:24][CH2:25][F:26])[CH2:21]3)=[CH:15][C:14]=2[O:27][CH3:28])[N:11]=1.C(N(C(C)C)CC)(C)C.C(Cl)Cl.[C:47](Cl)(=[O:50])[CH:48]=[CH2:49]>C1COCC1>[F:26][CH2:25][CH2:24][N:22]1[CH2:23][CH:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]3[N:11]=[C:6]([O:5][C:4]4[CH:3]=[C:2]([NH:1][C:47](=[O:50])[CH:48]=[CH2:49])[CH:34]=[CH:33][CH:32]=4)[C:7]4[CH:31]=[CH:30][NH:29][C:8]=4[N:9]=3)=[C:14]([O:27][CH3:28])[CH:15]=2)[CH2:21]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 86709977N1-(4-(3-aminophenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-N4-(1-(2-fluoroethyl)azetidin-3-yl)-2-methoxybenzene-1,4-diamine

Product 1

HCID 72949055N-(3-(2-(4-(1-(2-fluoroethyl)azetidin-3-ylamino)-2-methoxyphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl) acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL-round-bottom flask with a magnetite was charged with N1-(4-(3-aminophenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-N4-(1-(2-fluoroethyl)azetidin-3-yl)-2-methoxybenzene-1,4-diamine (125 mg, 0.27 mmol), diisopropylethylamine (43 mg, 0.33 mmol) and DCM (20 mL). The mixture was cooled with an ice bath until the temperature was below 0° C., and a solution of acryloyl chloride (33 mg, 0.33 mmol) in THF (2 mL) was added dropwise over 5 minutes. The title compound is isolated and purified by preparative HPLC or preparative LC/MS, or by other standard purification techniques.

Workup

  1. temperatureThe mixture was cooled with an ice bath until the temperature
  2. customwas below 0° C.

Sources & evidence

ORD record
ord-1f159d859bc24a1fa5dc45f8f772a89a
Source dataset
uspto-grants-2014_04
Patent number
US08685988B2

Reaction notes

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