Water → HCID 69225804, compound

HRID 2250429Notes

Reaction equation

HRID 2250429 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]([OH:16])=O)[NH:11][C:8]2=[N:9][CH:10]=1)=[O:4].Cl.[CH:18]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)([CH3:20])[CH3:19].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.O>CN(C=O)C.CCN(CC)CC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14](=[O:16])[NH:27][CH:24]3[CH2:25][CH2:26][N:21]([CH:18]([CH3:20])[CH3:19])[CH2:22][CH2:23]3)[NH:11][C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 230334601-Isopropylpiperidin-4-amine hydrochlorideHCID 692285171H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid, 5-Methyl ester

Product 1

HCID 69225804HCID 69225804, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 9.5 g 1H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid 5-methyl ester in 120 mL DMF and 23.9 mL NEt3, 9.2 g 1-Isopropyl-piperidin-4-ylamine hydrochloride and 11 g BOP-Cl were added at RT and the mixture was stirred for 3 h. After addition of 20 mL of water the reaction mixture was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (1×50 ml) and then dried over MgSO4. After filtration the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel eluting with EtOAc/MeOH 9:7->EtOAc/MeOH/NH3(aq.) 6:4:0.04. The fractions containing the product were evaporated and codestilled with toluene. Yield: 7.2 g.

Workup

  1. extractionwas extracted with ethyl acetate (3×150 ml)
  2. washThe combined organic layers were washed with brine (1×50 ml)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration the solvent
  5. customwas removed under reduced pressure
  6. customthe residue was purified by chromatography on silica gel eluting with EtOAc/MeOH 9:7->EtOAc/MeOH/NH3(aq.) 6:4:0.04
  7. additionThe fractions containing the product
  8. customwere evaporated

Sources & evidence

ORD record
ord-8448036e8b31489db53dd05c006107f3
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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