Diisopropylethylamine → HCID 25099476, compound

HRID 2381903Notes

Reaction equation

HRID 2381903 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:51][C:52]1[CH:53]=[C:54]2[C:58](=[CH:59][CH:60]=1)[N:57]([NH2:61])[CH:56]=[C:55]2[CH3:62]>CN(C=O)C.O.CCOC(C)=O>[F:51][C:52]1[CH:53]=[C:54]2[C:58](=[CH:59][CH:60]=1)[N:57]([NH:61][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[N:5][CH:6]=1)=[O:10])[CH:56]=[C:55]2[CH3:62]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 457912394-Methyl-2-(pyridin-3-yl)pyrimidine-5-carboxylic acidHCID 68554957HCID 68554957, compound

Product 1

HCID 25099476HCID 25099476, compoundYield 21.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (502 mg, 2.33 mmol), HCTU (1.054 g, 2.55 mmol), and DIPEA (1.10 mL, 6.30 mmol) in DMF (10 mL) is stirred at rt under N2 for 10 min. 5-Fluoro-3-methyl-indol-1-ylamine (341 mg, 2.08 mmol) is added. The resulting mixture is stirred at rt overnight. The mixture is portioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is triturated in ether (4 times) to afford 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide (160 mg, 21%) as a solid. MS: 362 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 11.86 (s, 1H), 9.58 (s, 1H), 9.24 (s, 1H), 8.79-8.78 (m, 1H), 8.74 (td, 1H), 7.62 (dd, 1H), 7.44 (dd, 1H), 7.37-7.36 (m, 2H), 7.06 (td, 1H), 2.78 (s, 3H), 2.27 (s, 3H).

Workup

  1. customThe organic phase is separated
  2. washwashed with saturated aqueous NaHCO3, water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated in ether (4 times)

Sources & evidence

ORD record
ord-a32af42f7d564e659df8dda1ac4b2739
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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