Water → HCID 90052394, compound

HRID 2284769Notes

Reaction equation

HRID 2284769 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1[C:18]([NH:32][CH2:33][CH2:34][CH2:35]O)=[N:19][C:20]([NH:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)=[N:21][CH:22]=1.O.C(OCC)(=O)C>C(Cl)Cl.COCCN(S(F)(F)F)CCOC>[N:32]1([C:18]2[C:17]([C:16]#[C:15][CH2:14][CH2:13][CH2:12][N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])=[CH:22][N:21]=[C:20]([NH:23][C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=3)[N:19]=2)[CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 90052151HCID 90052151, compound

Product 1

HCID 90052394HCID 90052394, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideSolvent

Procedure

To a suspension of 4-((5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)-4-((3-hydroxypropyl)amino)pyrimidin-2-yl)amino)benzonitrile (J15, 51 mg) in methylene chloride (1 mL), bis(2-methoxyethyl)aminosulfur trifluoride (188 μL) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, water and ethyl acetate were added. The solid matter was taken by filtration, washed successively with water and ethyl acetate, and then dried under reduced pressure to obtain 4-((4-(azetidin-1-yl)-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrile (J16, 48 mg) as pale yellow solid.

Workup

  1. additionwas added under ice cooling
  2. filtrationThe solid matter was taken by filtration
  3. washwashed successively with water and ethyl acetate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7614f64c717e4aad84e6cf59dffccb3a
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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