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

HRID 2093109Notes

Reaction equation

HRID 2093109 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[N:16]([CH3:17])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]1(N=C=NC2CCCCC2)CCCCC1.[OH:36][C:37]1[C:45]2[N:44]=N[NH:42][C:41]=2[CH:40]=[CH:39][CH:38]=1.[C:46]1([NH2:53])[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[NH2:52].CN([CH:57]=[O:58])C>O>[NH2:42][C:41]1[CH:40]=[CH:39][CH:38]=[CH:37][C:45]=1[NH:44][C:18]([C:15]1[N:16]([CH3:17])[C:10]2[CH2:9][NH:8][CH2:13][CH2:12][C:11]=2[CH:14]=1)=[O:20].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([C:18](=[O:19])[NH:52][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=3[NH:53][C:57]([O:36][C:37]([CH3:45])([CH3:21])[CH3:38])=[O:58])[N:16]([CH3:17])[C:10]=2[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 668646696-(tert-butoxycarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidHCID 178418300HCID 178418300, compound

Product 2

HCID 668639302-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,5,7-tetrahydro-pyrrolo[2,3-c]pyridine-6-carboxylic acid tert-butyl esterHCID 66864727N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of compound 6-(tert-butoxycarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1.0 eq) in DMF was added Dicyclohexyl carbo diimide (1.3 eq.) and hydroxy benzotriazole (1.3 eq) and reaction was stirred for 1 hr. followed by addition of monoboc protected phenylene diamine. The reaction was stirred further for 48 hrs. Water was added and reaction mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired compound 2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,5,7-tetrahydro-pyrrolo[2,3-c]pyridine-6-carboxylic acid tert-butyl ester which was treated with ethereal HCl to afford the hydrochloride salt of the base which was then neutralized to obtained the N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide.

Workup

  1. additionfollowed by addition of monoboc
  2. stirringThe reaction was stirred further for 48 hrs
  3. customreaction mixture
  4. extractionwas extracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

Sources & evidence

ORD record
ord-ccf1874c872840d59696967a67beb919
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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