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

HRID 2281504노트

반응식

HRID 2281504 반응식
[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][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)[CH2:15][CH2:14]1.O>C(Cl)Cl.CN(C=O)C>[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][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)[CH2:17][CH2:18]1)=[O:6])#[N:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 579903404-(4-(piperidin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

생성물 1

HCID 579904384-(4-(1-(2-cyanoacetyl)piperidin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide수율 41.9%

시약·촉매·용매 2

HCID 6344Dichloromethane촉매HCID 6228Dimethylformamide용매

실험 절차

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)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (20 mg, 0.057 mmol) and TEA (0.450 mL, 3.22 mmol) in DMF (2 mL) was added. The mixture was stirred at room temperature for 20 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 200.0, 311.9 nm.

후처리

  1. additionwas added
  2. temperatureTo the above solution cooled in an ice bath
  3. stirringThe mixture was stirred at room temperature for 20 h
  4. customCH2Cl2 was removed in vacuo
  5. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-e40d3f076dd446ce923e690d22fc8618
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139581B2

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