HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dicyclohexylcarbodiimide → 2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 2093097
Notes
Print preview

Reaction equation

HRID 2093097 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:20])[C:15]([C:17]([OH:19])=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[C:46]([NH:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[NH2:60])([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:20])[C:15]([C:17](=[O:19])[NH:60][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=3[NH:53][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 665232975-((tert-butoxy)carbonyl)-1-methyl-1H,4H,5H,6H,7H-pyrrolo(3,2-c)pyridine-2-carboxylic acid

Product 1

HCID 668639202-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 5-(tert-butoxycarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (1.0 eq) in DMF was added DCC (1.3 eq.), and HOBt (1.3 eq) and stirred for 1 hr. Monoboc phenylene diamine was added and reaction was stirred for 48 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 2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester which was then reacted with hydrochloric acid saturated diethyl ether to get N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxamide.

Workup

  1. customreaction
  2. stirringwas stirred for 48 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-928edc39e0244993a65986b09652d3b3
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440830B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes