Hydrochloric Acid → 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 1821810노트

반응식

HRID 1821810 반응식
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:23]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[NH:15][C:14]=12)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68982508HCID 68982508, 화합물

생성물 1

HCID 689809557-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid수율 22%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of ethyl 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (Reference Example 3) (500 mg, 1.30 mmol), 2 M sodium hydroxide solution (6 mL), tetrahydrofuran (3 mL) and ethanol (3 mL) was refluxed for 2 h. The mixture was neutralized by addition of 1 M hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was crystallized from ethyl acetate to give 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (100 mg, 22%) as pale brown amorphous solid. Additional material (348 mg, 75%; 97% overall yield) was obtained from the mother liquid: Rf 0.01 (silica gel, ethyl acetate); mp 114-120° C.; 1H NMR (300 MHz, DMSO-d6) δ4.82 (4H, br s), 7.18-7.35 (12H, m), 7.68 (1H, d, J=6.0 Hz); ESI MS m/z 358 [C22H19N3O2+H]+; HPLC (Method A) 98.8% (AUC), tR=17.7 min.

후처리

  1. temperaturewas refluxed for 2 h
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-818cd2f4c05a42d2b9083897ced212be
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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