Trimethylamine → 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

HRID 1485488노트

반응식

HRID 1485488 반응식
[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1.Cl.CN.[CH2:24]([N:26]=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CN(C)C>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:26][CH3:24])=[O:17])[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1

참가 물질

8

반응물 5

HCID 1146TrimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6364545Methylamine hydrochlorideHCID 866756513-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 866756523-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide수율 89.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid (300 mg, 0.98 mmol) was dissolved in N,N-dimethylformamide (5 mL) and then methylamine hydrochloride (329 mg, 4.91 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol), hydroxybenzotriazole (239 mg, 1.76 mmol) and trimethylamine (0.889 mL, 6.38 mmol) were added. The reaction mixture was stirred at room temperature for a day. The reaction mixture was diluted with ethyl acetate and then washed with ammonium chloride aqueous solution. The organic layer was dried with magnesium sulfate, filtered with celite and then concentrated. Purification by chromatography (1/4 ethyl acetate/hexane) yielded the target compound (280 mg, 89% yield).

후처리

  1. washwashed with ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered with celite
  4. concentrationconcentrated
  5. customPurification by chromatography (1/4 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-cddbe8c3fc1f4e6f89228ca4466d3637
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422307B2

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