Ethyl orthoformate → 1-Cyclohexyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine

HRID 1969801Notes

Reaction equation

HRID 1969801 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[NH:15][CH:16]=[CH:17][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:18](OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH:1]1([N:7]2[C:8]3=[C:9]4[CH:17]=[CH:16][NH:15][C:10]4=[N:11][CH:12]=[C:13]3[N:14]=[CH:18]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrate3×HCID 58557425N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

Product 1

HCID 583950441-Cyclohexyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridineYield 2.3%

Conditions

Temperature
80 °C

Procedure

To a solution of N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.084 g, 0.36 mmol) in triethyl orthoformate (1 mL, 6 mmol) was added p-toluenesulfonic acid monohydrate (0.002 g, 0.011 mmol). The reaction mixture was heated at about 80° C. for about 1 h. p-Toluenesulfonic acid monohydrate (0.002 g, 0.011 mmol) was added and the reaction mixture was stirred at about 80° C. After about 1 h, p-toluenesulfonic acid monohydrate (0.002 g, 0.011 mmol) was added and the reaction mixture was stirred at about 80° C. for about 2 h. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The reaction was purified by RP-HPLC (Table 1, Method m) to give 1-cyclohexyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine (0.002 g, 2%) as a brown solid: LC/MS (Table 1, Method a) Rt=1.90 min; MS m/z 241 (M+H)+.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at about 80° C. for about 2 h
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customThe reaction was purified by RP-HPLC (Table 1, Method m)

Sources & evidence

ORD record
ord-a1873f87a0d34b1abc5f21b77a9a1a29
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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