Hydrochloric Acid → HCID 57636055, compound

HRID 216232Notes

Reaction equation

HRID 216232 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-796169a6e9e74a1b9e91aa4b5c0cdb93
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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