Water → HCID 57990268, compound

HRID 2381733Notes

Reaction equation

HRID 2381733 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][CH2:16][CH:15]([NH:19][C:20]2[C:21]3[CH:38]=[CH:37][NH:36][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)[CH2:14]1.O>C(Cl)Cl.CN(C=O)C>[C:1]([CH2:3][C:4]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([NH:19][C:20]2[C:21]3[CH:38]=[CH:37][NH:36][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)[CH2:14]1)=[O:6])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 57990316HCID 57990316, compound

Product 1

HCID 57990268HCID 57990268, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of cyanoacetic acid (46 mg, 0.54 mmol) in CH2Cl2 (1 mL) (containing 2 drops of DMF), oxalyl chloride (0.047 mL, 0.54 mmol) was added. The mixture was stirred at room temperature for 40 min. To the above solution cooled in an ice bath, a solution of 4-(4-(piperidin-3-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (18 mg, 0.051 mmol) and TEA (0.250 mL, 1.80 mmol) in DMF (2 mL) was added. The mixture was stirred for 2 h. Water was added. CH2Cl2 was removed in vacuo. The residue was purified by HPLC to give the titled compound (10 mg). MS 419.3 (M+H); UV 201.6, 311.9 nm.

Workup

  1. additionwas added
  2. temperatureTo the above solution cooled in an ice bath
  3. stirringThe mixture was stirred for 2 h
  4. customCH2Cl2 was removed in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9c9a537d8ca747a796e8e3aeb9ff6eba
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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