N,N-Diethyl-2-propanamine → 2-Pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridine-1-ylamide

HRID 2382013Notes

Reaction equation

HRID 2382013 reaction equation
C(N(CC)C(C)C)C.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][N:16]=1.[N:24]1([NH2:33])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=[CH:25]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:24]1([NH:33][C:21]([C:18]2[CH:19]=[N:20][C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=3)=[N:16][CH:17]=2)=[O:23])[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[CH:26]=[CH:25]1

Participants

6

Reactant 4

HCID 521913N,N-Diethyl-2-propanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 52239501H-Pyrrolo[2,3-b]pyridin-1-amineHCID 249036332-(Pyridin-2-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 591999572-Pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridine-1-ylamideYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl-iso-propylamine (1.13 mmol) is added a solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[2,3-b]pyridine-1-ylamine (0.75 mmol) and TBTU in anhydrous DMF (7 mL) at rt, and the reaction mixture is stirred at 80° C. overnight. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water twice, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to give a crude product. The product is crystallized from EtOAc to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridine-1-ylamide (78 mg, 25%) as a solid. MS: 317 (M+H); 1H NMR (300 MHz, CD3OD): δ 6.56 (m, H) 7.24 (m, H), 7.53 (m, H), 7.61 (m, H), 8.01-8.17 (m, 2H), 8.27 (d, H), 8.69 (m, H), 8.78(m, H), 9.51 (s, 2H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with water twice
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 10% MeOH in DCM
  9. customto give a crude product
  10. customThe product is crystallized from EtOAc

Sources & evidence

ORD record
ord-4661879e8fd548988b4677d5f4fb56c8
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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