N,N-Diethyl-2-propanamine → HCID 59200054, compound

HRID 2382014Notes

Reaction equation

HRID 2382014 reaction equation
C(N(CC)C(C)C)C.[CH3:9][C:10]1[C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:11]=1.[N:25]1([NH2:34])[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[CH:27]=[CH:26]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:25]1([NH:34][C:16]([C:15]2[C:10]([CH3:9])=[N:11][C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:13][CH:14]=2)=[O:18])[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[CH:27]=[CH:26]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 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 59200054HCID 59200054, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl-iso-propylamine (1.13 mmol) is added a solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[2,3-b]pyridine-1-ylamine (0.75 mmol) and TBTU (0.9 mmol) 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 saturated aqueous Na2CO3 and water, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% CH3CN in DCM to give a crude product. The crude product is crystallized from EtOAc to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[2,3-b]pyridine-1-ylamide (95 mg, 38%) as a solid. MS: 331 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.89 (s, 3H), 6.65 (d, H), 7.23 (m, H), 7.48-7.66 (m, 2H), 8.01-8.15 (m, 2H), 8.29 (m, H), 8.64 (d, H), 8.77 (d, H), 9.33 (s, 2H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with saturated aqueous Na2CO3 and water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 10% CH3CN in DCM
  9. customto give a crude product
  10. customThe crude product is crystallized from EtOAc

Sources & evidence

ORD record
ord-5c128a49ae4f4e759183e549a38f6749
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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