Hydrochloric Acid → HCID 86687793, compound

HRID 2280982Notes

Reaction equation

HRID 2280982 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])=[C:4]([F:17])[CH:3]=1.Cl[C:19]1[N:24]=[C:23]([NH:25][CH:26]2[CH2:28][CH2:27]2)[C:22]([C:29]([F:32])([F:31])[F:30])=[CH:21][N:20]=1.Cl>CCCCO>[CH:26]1([NH:25][C:23]2[C:22]([C:29]([F:31])([F:32])[F:30])=[CH:21][N:20]=[C:19]([NH:1][C:2]3[C:7]([OH:8])=[CH:6][C:5]([C:9]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)=[O:10])=[C:4]([F:17])[CH:3]=3)[N:24]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58459927HCID 58459927, compoundHCID 86687792HCID 86687792, compound

Product 1

HCID 86687793HCID 86687793, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4-amino-2-fluoro-5-hydroxyphenyl)(morpholino)methanone (200 mg, 0.83 mmol), 2-chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (198 mg, 0.83 mmol), concentrated HCl (0.1 mL), and n-BuOH (10 mL) was stirred at 100° C. for 10 h. The mixture was concentrated under reduced pressure and the residue was purified by rp-HPLC to afford the title compound as white solid (125 mg, 34%); 1H NMR (500 MHz, DMSO) δ 8.55-8.49 (m, 1H), 8.26 (s, 1H), 8.18-8.08 (m, 1H), 7.45 (br s, 1H), 6.77 (d, J=7.0 Hz, 1H), 3.62-3.53 (m, 4H), 3.48-3.46 (m, 2H), 3.30-3.11 (m, 2H), 2.84-2.82 (m, 1H), 0.84-0.78 (m, 2H), 0.75-0.68 (m, 2H); LCMS: m/z=442.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by rp-HPLC

Sources & evidence

ORD record
ord-dc273bf43d9242cca3e0be1797dee07d
Source dataset
uspto-grants-2015_09
Patent number
US09139566B2

Reaction notes

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