N,N-Diethyl-2-propanamine → HCID 59200062, compound

HRID 2382017Notes

Reaction equation

HRID 2382017 reaction equation
C(N(CC)C(C)C)C.[F:9][C:10]1[CH:11]=[C:12]([C:16]2[N:21]=[C:20]([CH3:22])[C:19]([C:23]([OH:25])=O)=[CH:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1.[N:26]1([NH2:35])[C:30]2=[CH:31][N:32]=[CH:33][CH:34]=[C:29]2[CH:28]=[CH:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[N:26]1([NH:35][C:23]([C:19]2[C:20]([CH3:22])=[N:21][C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=3)=[N:17][CH:18]=2)=[O:25])[C:30]2=[CH:31][N:32]=[CH:33][CH:34]=[C:29]2[CH:28]=[CH:27]1

Participants

7

Reactant 4

HCID 521913N,N-Diethyl-2-propanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 68555938HCID 68555938, compound

Product 1

HCID 59200062HCID 59200062, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl-iso-propylamine (1.13 mmol) is added a solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[2,3-c]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. Water is added and the mixture is extracted with EtOAc. The organic layer is separated, washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 40-100% MeOH in DCM to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide (117 mg, 45%) as a solid. MS: 348 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.84 (s, 3H), 6.72 (d, H), 7.29 (m, H), 7.55 (m, H), 7.71 (m, H), 8.14-8.29 (m, 2H), 8.36 (d, 3), 8.75 (s, H), 9.17 (s, H). IC50=28.5 nM.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. customThe organic layer is separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 40-100% MeOH in DCM

Sources & evidence

ORD record
ord-9a68468d866b4d889be5aa7a42a36653
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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