Diisopropylethylamine → HCID 58382087, compound

HRID 1628002Notes

Reaction equation

HRID 1628002 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][NH:10][CH3:11])=[CH:6][N:5]=[C:4]2[N:12]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:14][C:3]=12.CCN(C(C)C)C(C)C>C(O)CC>[CH3:11][N:10]1[C:2]2=[C:3]3[CH:14]=[CH:13][N:12]([S:15]([C:18]4[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=4)(=[O:17])=[O:16])[C:4]3=[N:5][CH:6]=[C:7]2[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 67216563HCID 67216563, compound

Product 1

HCID 58382087HCID 58382087, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

2-(4-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methylethanamine (0.670 g, 1.84 mmol) in PrOH (20 mL) was heated to about 105° C. for about 44 h. DIEA (0.39 mL, 2.2 mmol) was added and heating was continued at about 105° C. for about 24 h. The mixture was cooled to rt and the solvent was evaporated under reduced pressure. The material was treated with saturated NaHCO3 (15 mL) and water (10 mL) then extracted with DCM (25 mL then 10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by flash chromatography on 10 g of silica with EtOAc as an eluent to give 1-methyl-6-tosyl-1,2,3,6-tetrahydrodipyrrolo[2,3-b:2′,3′-d]pyridine (0.308 g, 51%): LC/MS (Table 2, Method a) Rt=2.53 min; MS m/z 328 (M+H)+.

Workup

  1. temperatureheating
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe material was treated with saturated NaHCO3 (15 mL) and water (10 mL)
  4. extractionthen extracted with DCM (25 mL
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was purified by flash chromatography on 10 g of silica with EtOAc as an eluent

Sources & evidence

ORD record
ord-7e841cf3d13f420b9942fadbd67dc43e
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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