Water → 4-(4-(1-(2-cyanoacetyl)piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

HRID 2381728Notes

Reaction equation

HRID 2381728 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[C:21]3[CH:38]=[CH:37][N:36]([S:39]([C:42]4[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=4)(=[O:41])=[O:40])[C:22]=3[N:23]=[C:24]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[CH:29][CH:28]=3)[N:25]=2)[CH2:15][CH2:14]1.O>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[C:1]([CH2:3][C:4]([N:13]1[CH2:14][CH2:15][CH:16]([NH:19][C:20]2[C:21]3[CH:38]=[CH:37][N:36]([S:39]([C:42]4[CH:43]=[CH:44][C:45]([CH3:46])=[CH:47][CH:48]=4)(=[O:41])=[O:40])[C:22]=3[N:23]=[C:24]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[CH:29][CH:28]=3)[N:25]=2)[CH2:17][CH2:18]1)=[O:6])#[N:2]

Participants

8

Reactant 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 579903604-(4-(piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

Product 1

HCID 579904094-(4-(1-(2-cyanoacetyl)piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamideYield 71.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of cyanoacetic acid (85 mg, 1.00 mmol) in CH2Cl2 (2 mL) (containing 2 drops of DMF), oxalyl chloride (0.082 mL, 0.94 mmol) was added. The mixture was stirred at room temperature for 50 min. To the above solution cooled in an ice bath, a solution of 4-(4-(piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (58 mg, 0.11 mmol) and TEA (0.450 mL, 3.22 mmol) in DMF (2 mL) was added. The mixture was stirred for 2 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 4-(4-(1-(2-cyanoacetyl)piperidin-4-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (45 mg).

Workup

  1. additionwas added
  2. temperatureTo the above solution cooled in an ice bath
  3. stirringThe mixture was stirred for 2 h
  4. customThe organic phase was separated
  5. washwashed with 5% NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94805943c09949c189eb59514a575d4e
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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