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ノート

反応式

HRID 2093119 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-21c41703363e443fb79a2154fcdd4574
出典データセット
uspto-grants-2013_05
特許番号
US08440830B2

反応ノート

読み込み中…