Potassium Carbonate → 3-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

HRID 1066769노트

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HRID 1066769 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1.[Cl:13]N1C(=O)CCC1=O.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O.ClCCl>[NH2:1][C:2]1[C:3]([Cl:13])=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

생성물 1

HCID 211964063-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine D4 (900 mg, 5.52 mmol) was dissolved in acetic acid (50 ml) before being treated portionwise with N-chlorosuccinimide (1.11 g, 8.28 mmol) 20 min. The reaction mixture was stirred overnight at room temperature under argon. The reaction mixture was diluted with water (125 ml), basified to pH10 with solid K2CO3 and extracted with dichloromethane (×2). The combined organic extracts were washed with sodium bicarbonate, dried (MgSO4) and evaporation in vacuo gave a crude black solid. Flash chromatography using dichloromethane (10% MeOH) gave thetitle compound as a pale orange solid.

후처리

  1. extractionextracted with dichloromethane (×2)
  2. washThe combined organic extracts were washed with sodium bicarbonate
  3. customdried
  4. custom(MgSO4) and evaporation in vacuo
  5. customgave a crude black solid
  6. customgave thetitle compound as a pale orange solid

출처 및 근거

ORD 기록
ord-d5c6bf76fcfc4e3797ab47b3513e3f4d
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06245778B1

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