Hydrochloric Acid → HCID 57636055, compound

HRID 2110760Notes

Reaction equation

HRID 2110760 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][NH:12][C:13]1[N:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([C:21]2[CH:22]=[C:23]([C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29])[CH:24]=[CH:25][CH:26]=2)[CH:14]=1.[CH2:33](O)[CH3:34]>>[CH2:33]([O:29][C:28](=[O:30])[C:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:15]2[CH:14]=[C:13]([NH:12][CH2:11][CH2:10][C:4]3[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=3[Cl:2])[N:18]=[C:17]([O:19][CH3:20])[N:16]=2)[CH:22]=1)([F:31])[F:32])[CH3:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11540010HCID 11540010, compound

Product 1

HCID 57636055HCID 57636055, compound

Conditions

Temperature
65 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane, 52 μL, 2.1 mmol) is added to a solution of (3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-difluoro-acetic acid [65 mg, 0.14 mmol, Example 81(a)] in ethyl alcohol (6 mL) and the reaction mixture is stirred overnight at 65° C. The reaction is cooled to room temperature, quenched with water, extracted twice with ethyl acetate. The combined extracts are dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by chromatography to afford (3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-difluoro-acetic acid ethyl ester [18 mg, Example 81(c)]. LCMS: RT=3.19 minutes; MS: 496, 498 (M+H); 1H NMR [300 MHz, CDCl3]: □8.18 (2H, d, J=3.5 Hz), 7.7 (1H, d, J=3.5 Hz), 7.55 (1H, t, J=3.5 Hz), 7.4 (1H, s), 7.42 (1H, s), 7.18 (2H, s), 6.45 (1H, s), 5.08 (1H, b), 4.3 (2H, q, J=4 Hz), 4.05 (3H, s), 3.72 (2H, b), 3.08 (2H, t, J=3.5 Hz), 1.3 (3H, t, J=4 Hz).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customquenched with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-5f876f275ba9450ea0088261c4c88902
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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