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Hydrochloric Acid → Tert-butyl 2,4-dimethoxybenzyl6-amino-1-methyl-1h-imidazo[4,5-c]pyridin-4-ylcarbamate

HRID 220341
Notes
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Reaction equation

HRID 220341 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:4]=1[CH2:5][N:6]([C:14]1[C:19]2[N:20]=[CH:21][N:22]([CH3:23])[C:18]=2[CH:17]=[C:16]([N:24]=C(C2C=CC=CC=2)C2C=CC=CC=2)[N:15]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Cl>C1COCC1>[NH2:24][C:16]1[N:15]=[C:14]([N:6]([CH2:5][C:4]2[CH:38]=[CH:39][C:40]([O:42][CH3:43])=[CH:41][C:3]=2[O:2][CH3:1])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:19]2[N:20]=[CH:21][N:22]([CH3:23])[C:18]=2[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58180611tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate

Product 1

HCID 58180570Tert-butyl 2,4-dimethoxybenzyl6-amino-1-methyl-1h-imidazo[4,5-c]pyridin-4-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 1000 mL round bottom flask, tert-butyl 2,4-dimethoxybenzyl(6-(diphenylmethyleneamino)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)carbamate (example 1C, 9.2 g, 15.93 mmol) was stirred in THF (50 mL). 1 N HCl (33 mL) was added. After 2 min, the reaction was quenched with 1 N NaOH (65 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dried under vacuum for 1 h and triturated with ether (4×). Isolated tert-butyl 6-amino-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(2,4-dimethoxybenzyl)carbamate (6.587 g, 15.93 mmol, 100% yield) as a cream solid. Material carried forward with no further purification.

Workup

  1. customthe reaction was quenched with 1 N NaOH (65 mL) and ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was dried under vacuum for 1 h
  7. customtriturated with ether (4×)

Sources & evidence

ORD record
ord-9eb6dc8c6b9f4cbd8c3050c4aac9435e
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes