Hydrochloric Acid → HCID 178496114, compound

HRID 2189165Notes

Reaction equation

HRID 2189165 reaction equation
[CH3:1][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][CH2:25][O:26][CH3:27])[NH:14][C:13](=[O:28])[N:12]=3)[CH:9]=2)[N:4](C(=O)C)[N:3]=1.Cl.OCCOC1C=CC=CC=1C1NC(=O)N=C(C2C=C3C(=CC=2)NN=C3C)C=1>CO>[OH:26][CH2:25][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[CH3:1])[CH:16]=1.[CH3:1][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][CH2:25][O:26][CH3:27])[NH:14][C:13](=[O:28])[N:12]=3)[CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68603919HCID 68603919, compoundHCID 178434228HCID 178434228, compound

Product 1

HCID 178496114HCID 178496114, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A flask was charged with 4-(3-methyl-1-acetyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (2.50 g, 6.2 mmol), MeOH (60 mL) and 10 ml of 4 N HCl in dixoane (Aldrich). The mixture was heated at 60° C. overnight. The reaction was concentrated, and the residue was submitted to preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate) to result in 4-(3-methyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (1.32 g). 1H NMR (400 MHz, d6-DMSO): δ 12.90 (s, br, 1H), 11.75 (s, br, 1H), 8.60 (s, 1H), 8.15 (d, 1H), 7.75 (d, 1H), 7.60-7.45 (m, 3H), 7.25-7.10 (m, 2H), 4.20 (t, 2H), 3.75 (t, 2H), 3.40 (s, 3H), 2.60 (s, 3H). MS (EI) for C21H20N4O3: 377 (MH+); and 6-{2-[(2-hydroxyethyl)oxy]phenyl}-4-(3-methyl-1H-indazol-5-yl)pyrimidin-2(1H)-one (250 mg) 1H NMR (400 MHz, d6-DMSO): δ 8.88 (s, 1H), 8.09 (d, 1H), 7.80-7.45 (m, 4H), 7.35-7.05 (m, 2H), 4.23 (t, 2H), 3.80 (t, 2H), 2.40 (s, 3H). MS (EI) for C20H18N4O3: 363 (MH+).

Workup

  1. concentrationThe reaction was concentrated
  2. customto result in 4-(3-methyl-1H-indazol-5-yl)-6-(2-{[2-(methyloxy)ethyl]oxy}phenyl)pyrimidin-2(1H)-one (1.32 g)

Sources & evidence

ORD record
ord-6df2429ca4124b66adb47d865ea46180
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

Loading…