Formaldehyde → HCID 67278388, compound

HRID 1696258Notes

Reaction equation

HRID 1696258 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=O.[CH3:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[C:19]2=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=[C:18]2[NH:17][C:16]1=[O:27]>>[CH3:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[C:19]2=[C:20]3[C:26]([CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:25][NH:24][C:21]3=[N:22][CH:23]=[C:18]2[NH:17][C:16]1=[O:27]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 15953425HCID 15953425, compound

Product 1

HCID 67278388HCID 67278388, compound

Procedure

To a solution of pyrrolidine (0.0184 mL) in ACOH (0.6 mL) was added paraformaldehyde (7.8 mg), and stirred at ambient temperature for 5 minutes. To the mixture was added 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (30 mg), and stirred at 85° C. for 8 hours, then stirred at ambient temperature for 14 hours. AcOH was removed in vacuo, and the residue was diluted with tetrahydrofuran, then basified with saturated aqueous sodium hydrogencarbonate. The mixture was extracted with EtOAc, washed with 10% NaCl solution, and brine, dried over MgSO4, evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1 to 10:1) to give 1-[(1S,2R)-2-methylcyclohexyl]-8-(1-pyrrolidinylmethyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (32.7 mg) as a pale yellow amorphous solid.

Workup

  1. stirringstirred at 85° C. for 8 hours
  2. stirringstirred at ambient temperature for 14 hours
  3. customAcOH was removed in vacuo
  4. additionthe residue was diluted with tetrahydrofuran
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with 10% NaCl solution, and brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (chloroform:methanol=15:1 to 10:1)

Sources & evidence

ORD record
ord-0dce0c3d1d414baabac396691c2a1c3c
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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