Trimethyl orthoformate → HCID 178452905, compound

HRID 1909047Notes

Reaction equation

HRID 1909047 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:20])[N:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:22]OC(OC)OC.C([O-])(O)=O.[Na+]>C1(S(O)(=O)=O)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH2:12][CH2:11][N:10]([C:13]2[N:14]=[C:15]3[NH:20][CH:22]=[N:19][C:16]3=[CH:17][CH:18]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 66599421HCID 66599421, compound

Product 1

HCID 178452905HCID 178452905, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 7371Benzenesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

The solution of [1-(5,6-diamino-pyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (2 g, 6.82 mmole), trimethylorthoformate (3.83 g, 25.9 mmole), benzenesulfonic acid (43 mg, 0.27 mmole) and toluene (100 ml) was heated to reflux overnight. The reaction solution was basified with NaHCO3 and concentrated to afford crude [1-(3H-imidazo[4,5-b]pyridine-5-yl)-pyrrolin-3-yl]-carbamic acid tert-butyl ester (1.96 g, 94%) as a dark green solid. MS(ESI) m/z 304 [M+1].

Workup

  1. temperatureto reflux overnight
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f77faf24c0e4bacb085c867bd0ff487
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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