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Trifluoroacetic acid → 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

HRID 1188027
Notes
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Reaction equation

HRID 1188027 reaction equation
[CH:1]1([N:4]([CH:41]2[CH2:43][CH2:42]2)[C:5]([C:7]2[N:38]([CH2:39][CH3:40])[C:10]3=[N:11][C:12]([N:19](CC4C=CC(OC)=CC=4OC)C(=O)OC(C)(C)C)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:19][C:12]1[N:11]=[C:10]2[N:38]([CH2:39][CH3:40])[C:7]([C:5]([N:4]([CH:41]3[CH2:43][CH2:42]3)[CH:1]3[CH2:3][CH2:2]3)=[O:6])=[CH:8][C:9]2=[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58180545Tert-butyl 7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate

Product 1

HCID 581805034-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of tert-butyl 7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate (example 1I, 2.66 g, 4.51 mmol) in dichloromethane (33.8 mL) was added TFA (11.28 mL). The reaction mixture was stirred at rt 45 min and was concentrated in vacuo. The crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (2 x) and the combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude solid was purified by flash chromatography using an Isco 40 g column eluting with 4-10% MeOH/CH2Cl2 to yield 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (1.2 g, 3.55 mmol, 79% yield) as a pale yellow solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with ethyl acetate (2 x)
  4. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was purified by flash chromatography
  8. washeluting with 4-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-47486bf7257d4a0c90706f0b00154138
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673933B2

Reaction notes

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