Hydrochloric Acid → HCID 68687096, compound

HRID 1441323Notes

Reaction equation

HRID 1441323 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:32]=[CH:31][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([F:30])=[CH:17][N:16]=3)=[CH:12][C:11]=2[CH3:33])[CH2:6][CH2:5]1)(=O)C.O.Cl>C(O)(C)C>[N:7]1([C:10]2[CH:32]=[CH:31][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([F:30])=[CH:17][N:16]=3)=[CH:12][C:11]=2[CH3:33])[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68686334HCID 68686334, compound

Product 1

HCID 68687096HCID 68687096, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-{4-[4-(Acetyl)piperazin-1-yl]3-methylanilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-fluoropyrimidine (Example 116; 1.89 g, 4.19 mmol) was stirred and heated in isopropanol (20 ml), H2O (5 ml) and 33% hydrochloric acid (4 ml) at 90° C. for 10 hours. The solvent was evaporated under reduced pressure to give a residue which was partitioned between water and DCM, basified with sat. sodium hydrogen carbonate and the aqueous layer was extracted with DCM twice. The organics were combined, washed with brine, dried and evaporation of solvent to give the title compound as a crisp foam which was dried in vac oven overnight at 50° C. (1.53 g, 89%) NMR (400 MHz) 1.39 (d, 6H), 2.23 (s, 3H), 2.51 (s, 3H, under DMSO signal), 2.72 (m, 4H), 2.85 (m, 4H), 3.29 (s, 1H under H2O signal), 5.42 (septet, 1H), 6.95 (d, 1H), 7.30 (d, 1H), 7.35 (d, 1H), 7.40 (dd, 1H), 8.48 (d, 1H), 9.24 (s, 1H); 19F NMR (400 MHz) −149.59 (t, 1F); m/z 410.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a residue which
  3. customwas partitioned between water and DCM
  4. extractionthe aqueous layer was extracted with DCM twice
  5. washwashed with brine
  6. customdried
  7. customevaporation of solvent

Sources & evidence

ORD record
ord-19a5c282b19946d484d62fedff8a4982
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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