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

HRID 2093119Notes

Reaction equation

HRID 2093119 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-21c41703363e443fb79a2154fcdd4574
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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