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

HRID 1066769ノート

反応式

HRID 1066769 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5c6bf76fcfc4e3797ab47b3513e3f4d
出典データセット
uspto-grants-2001_06
特許番号
US06245778B1

反応ノート

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