Triethylamine → tert-butyl 2-({2-[(tert-butoxycarbonyl)amino]phenyl} carbamoyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-5-carboxylate

HRID 2093119

반응식

HRID 2093119 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O=C1N([ClH]P([ClH]N2CCOC2=O)=O)CCO1.[C:43]([NH:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH2:57])([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CN(C=O)C>[C:46]([O:45][C:43]([NH:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][C:17]([C:15]1[NH:14][C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]=2[CH:16]=1)=[O:19])=[O:44])([CH3:49])([CH3:47])[CH3:48]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 665233075-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

생성물 1

HCID 66864448tert-butyl 2-({2-[(tert-butoxycarbonyl)amino]phenyl} carbamoyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-5-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (1.0 eq) in DMF was added triethyl amine (2.2 eq), Bis (2-oxo-3-oxazolidinyl) phosphonic chloride (BOP, 1.2 eq.) and stirred for 1 hr. Monoboc phenylene diamine was added and reaction was stirred for 24 hrs. Reaction mixture was then quenched with water and extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. Crude mass was then purified by silica gel column chromatography to afford tert-butyl 2-({2-[(tert-butoxycarbonyl)amino]phenyl}carbamoyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-5-carboxylate, which was then reacted with hydrochloric acid saturated diethyl ether to get N-(2-aminophenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2]pyridine-2-carboxamide

후처리

  1. customreaction
  2. stirringwas stirred for 24 hrs
  3. customReaction mixture
  4. customwas then quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness
  8. customCrude mass was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-21c41703363e443fb79a2154fcdd4574
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440830B2

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