Propionic Acid → HCID 25119282, compound

HRID 2189156Notes

Reaction equation

HRID 2189156 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])[NH:14][C:13](=[O:28])[N:12]=3)[CH:9]=2)[NH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:38](O)(=[O:41])[CH2:39][CH3:40].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O>[CH3:27][CH:25]([CH3:26])[CH2:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]1[NH:14][C:13](=[O:28])[N:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[NH:1][C:38](=[O:41])[CH2:39][CH3:40])[CH:16]=1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 251213724-(3-amino-1H-indazol-5-yl)-6-(2-isobutoxyphenyl)pyrimidin-2(1H)-one

Product 1

HCID 25119282HCID 25119282, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of commercially available 4-(3-amino-1H-indazol-5-yl)-6-(2-isobutoxyphenyl)pyrimidin-2(1H)-one (60 mg, 0.15 mmol) in dimethylacetamide (4 mL) and diisopropylethylamine (130 pt, 0.76 mmol, 5 eq) was added propionic acid (56 μL, 0.76 mmol, 5 eq) followed by HATU (290 mg, 0.76 mmol, 5 eq). The reaction mixture was stirred at room temperature for 16 h. Formation of product was confirmed by LC/MS and the product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to yield 17 mg (26%) of the title compound: 1H-NMR (400 MHz, d6-DMSO): δ 11.85 (s, 1H), 8.79 (s, 1H), 8.28-8.35 (m, 1H), 7.64 (s, 1H), 7.49-7.58 (m, 1H), 7.20 (d, 1H), 7.08-7.13 (m, 1H), 6.63 (s, 2H), 4.07-4.14 (m, 1H), 3.83-3.91 (m, 2H), 3.15-3.19 (m, 1H), 2.93-3.03 (m, 2H), 1.95-2.08 (m, 1H), 1.14-1.21 (m, 3H), 0.90-0.96 (m, 6H). MS (EI) for C24H25N5O3: 431 (MH+).

Workup

  1. customthe product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)

Sources & evidence

ORD record
ord-5d10ac6afef641f8b55ea6754b417e8c
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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