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Diisopropylethylamine → 4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide

HRID 2381908
Notes
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Reaction equation

HRID 2381908 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])[C:56]([CH3:62])=[CH:55]2>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])[C:56]([CH3:62])=[CH:55]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 685544085-Fluoro-2-methyl-indol-1-ylamine

Product 1

HCID 250995144-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide
Yield 11%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (504 mg, 2.34 mmol), HCTU (1.06 g, 2.55 mmol), and DIPEA (1.11 mL, 6.30 mmol) in DMF (15 mL) is stirred at rt under N2 for 10 min. 5-Fluoro-2-methyl-indol-1-ylamine (346 mg, 2.11 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 purified by silica gel chromatography eluting with 70% EtOAc in heptane to afford 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide (82 mg, 11%) as a solid. MS: 362 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 11.80 (s, 1H), 9.59 (d, 1H), 9.29 (s, 1H), 8.80-8.73 (m, 2H), 7.63 (dd, 1H), 7.22 (dd, 1H), 7.28 (dd, 1H), 6.97 (dt, 1H), 6.35 (s, 1H), 2.79 (s, 3H), 2.37 (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 purified by silica gel chromatography
  7. washeluting with 70% EtOAc in heptane

Sources & evidence

ORD record
ord-3c9144421032470bb61fee9c451d82d0
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes