Hydrochloric Acid → HCID 9955128, compound

HRID 1369410Notes

Reaction equation

HRID 1369410 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:28]3[CH2:33][CH2:32][N:31](OCC)[CH2:30][C:29]3=C=O)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)=[CH:4][CH:3]=1.C[Si](I)(C)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]3)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 85247Trimethylsilyl iodide2×HCID 86585016HCID 86585016, compound

Product 1

HCID 9955128HCID 9955128, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6212ChloroformSolvent

Procedure

4-(4-Fluorophenyl)-5-(2-[1-(S)-phenylethyl]amino-4-pyrimidyl)-2-(4-ethoxy-carbonylpiperazin-1-yl)oxazole (130 mg; 0.251 mmol in CHCl3 (2.6 ml) is treated with trimethylsilyl iodide (0.113 ml; 0.83 mmol) at 60 C. After 3 h a second portion of trimethylsilyl iodide (0.113 ml; 0.83 mmol) is added and the reaction heated at 60 C for 21 h. 6 M HCl in 1-propanol (3 ml) is added to the reaction mixture, stirred until dissolution is complete and then poured on a saturated solution of Na2CO3.

Workup

  1. temperaturethe reaction heated at 60 C for 21 h

Sources & evidence

ORD record
ord-458cad983eb4415e88e6f4ae9cd6d7e6
Source dataset
uspto-grants-2003_06
Patent number
US06579874B2

Reaction notes

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