Hydrochloric Acid → 4-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid

HRID 1640242

반응식

HRID 1640242 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=[O:9])[CH:3]=1.Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:29](=[CH:30][CH:31]=1)[CH2:28][C:18]1([C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]1=[O:27])[CH2:17]2>CC(O)C>[O:27]=[C:19]1[NH:20][C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:26]2[C:18]21[CH2:17][C:16]1[C:29](=[CH:30][CH:31]=[C:14]([NH:13][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=3)[CH:15]=1)[CH2:28]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 12828947Methyl 4-bromopicolinateHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

생성물 1

HCID 581175174-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

0.17 g (0.79 mmol) methyl 4-bromo-pyridine-2-carboxylate and 17 μL (70 μmol) of a 4M aqueous hydrochloric acid solution were added to 0.20 g (0.78 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one in 5.0 mL of 2-propanol. The reaction mixture was refluxed for 2 h, then cooled to RT and evaporated down. The residue was taken up in THF and mixed with 0.50 mL (2.0 mmol) of a 4M aqueous NaOH solution and stirred overnight at RT. The reaction mixture was diluted with water, combined with 0.5 mL conc. HCl and the solvent was eliminated. The precipitated product was suction filtered and dried.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customevaporated down
  3. additionmixed with 0.50 mL (2.0 mmol) of a 4M aqueous NaOH solution
  4. additionThe reaction mixture was diluted with water
  5. filtrationfiltered
  6. customdried

출처 및 근거

ORD 기록
ord-3a962e5ce5be4740a9adb95fe821c143
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110575B2

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