Hydrochloric Acid → HCID 178436774, compound

HRID 1509057Notes

Reaction equation

HRID 1509057 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]4[NH:22][CH:23]=[C:24]([C:26]([O:28]C)=[O:27])[N:25]=4)=[CH:16][CH:15]=3)[C:10]([CH2:30][CH3:31])=[C:9]([CH3:32])[N:8]=2)=[CH:4][CH:3]=1.[Li+].[OH-].O.C1COCC1.Cl>O.CO>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]4[NH:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=4)=[CH:18][CH:19]=3)[C:10]([CH2:30][CH3:31])=[C:9]([CH3:32])[N:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178436773HCID 178436773, compound

Product 1

HCID 178436774HCID 178436774, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A 8-mL vial was charged with methyl 2-[[4-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl]-1H-imidazole-4-carboxylate (8 mg, 0.017 mmol, 1 eq.), LiOH/H2O (19 mg, 0.44 mmol, 26 eq.), THF (1 ml), MeOH (0.2 ml) and water (0.2 ml). The resulting mixture was stirred at 55° C. overnight. After cooling to room temperature, the mixture was added 2N HCl aq. to pH 6˜7. The precipitate was collected by filtration and washed with water. After drying, the title compound was obtained as a solid (4.8 mg, 62% yield). MW=453.94. 1H NMR (400 MHz, DMSO-d6) δ 8.52 (brs, 1H), 7.65 (m, 3H), 7.55 (d, J=4.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 2H), 7.16 (d, J=4.0 Hz, 1H), 3.97 (s, 2H), 2.73 (q, J=7.2 Hz, 2H), 2.49 (s, 3H), 1.09 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customAfter drying

Sources & evidence

ORD record
ord-7392641341d4480f97cd84d08bf2d541
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…