Hydrochloric Acid → HCID 25104492, compound

HRID 884647Notes

Reaction equation

HRID 884647 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[N:3]=1.[O:16]=[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24](B(O)O)=[CH:25][C:19]=2[O:18]1.C([O-])(O)=[O:30].[Na+].Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:4]1[NH:3][C:2](=[O:30])[N:7]=[C:6]([C:24]2[CH:23]=[CH:22][C:20]3[NH:21][C:17](=[O:16])[O:18][C:19]=3[CH:25]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57498047HCID 57498047, compoundHCID 59348976(2-Oxo-2,3-dihydro-1,3-benzoxazol-6-yl)boronic acid

Product 1

HCID 25104492HCID 25104492, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A round flask was charged with 2,4-dichloro-6-(2-chlorophenyl)pyrimidine (150 mg), 2-oxo-2,3-dihydrobenzo[d]oxazol-6-ylboronic acid (104 mg), Pd(dppf)Cl2(15 mg), 1 M NaHCO3 (0.5 mL) and THF (5 mL). The reaction mixture was stirred at 70° C. for 2 hours, then 4 mL of conc. HCl was added. The reaction was heated to 90° C. for 5 hours. The mixture was filtrated, concentrated and purified by prep-HPLC to give the product. 1H NMR (400 MHz, d6-DMSO): δ 11.00 (s, br, 2H), 7.81-7.75 (m, 2H), 7.62-7.43 (m, 3H), 7.12-7.00 (m, 3H). MS (EI) for C17H10ClN3O3: 339 (MH+).

Workup

  1. temperatureThe reaction was heated to 90° C. for 5 hours
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated
  4. custompurified by prep-HPLC
  5. customto give the product

Sources & evidence

ORD record
ord-05524fce01dc49d6b28a73a2ab975ebf
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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