Acetic Anhydride → HCID 178474854, compound

HRID 2053004Notes

Reaction equation

HRID 2053004 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C)C=O>[NH2:16][C:15]1[C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8][N:7]([C@H:5]3[CH2:4][C@H:3]([CH2:2][NH:1][C:31](=[O:33])[CH3:32])[CH2:6]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178511295HCID 178511295, compound

Product 1

HCID 178474854HCID 178474854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 50 mg (0.125 mmol) of trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine in 2 ml of anhydrous N,N-dimethylformamide is added 13 μl (0.138 mmol) of acetic anhydride (Fluka, Buchs, Switzerland). After stirring 1 h at RT, working-up is effected by partitioning between water and ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated to dryness to provide trans-N-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-acetamide. Analytical HPLC: tR=6.65 min (Grad 2); ES-MS: m/eo=442.0.

Workup

  1. customby partitioning between water and ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-746b02ec570440ccabdf640e03a76403
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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