Hydrochloric Acid → HCID 54689858, compound

HRID 1244152Notes

Reaction equation

HRID 1244152 reaction equation
[H-].[Na+].C(O[C:6]([C:8]1[C:12]([C:13]2[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:15]([Br:28])[CH:14]=2)=[CH:11][S:10][C:9]=1[NH:29][C:30](=[O:34])[CH2:31][C:32]#[N:33])=[O:7])C.Cl>C1COCC1>[CH2:21]([O:20][C:16]1[C:17]([Br:19])=[CH:18][C:13]([C:12]2[C:8]3[C:6]([OH:7])=[C:31]([C:32]#[N:33])[C:30](=[O:34])[NH:29][C:9]=3[S:10][CH:11]=2)=[CH:14][C:15]=1[Br:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69607327HCID 69607327, compound

Product 1

HCID 54689858HCID 54689858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (275 mg, 6.87 mmol) in THF (50 mL) was added 4-(4-benzyloxy-3,5-dibromo-phenyl)-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester from Example 36D (1.8 g, 3.12 mmol) in THF (50 mL). The reaction stirred at room temperature for 18 h. It was acidified with 1M HCl and concentrated in vacuo. The resulting orange solid was taken up in H2O and filtered, rinsing with H2O (2×20 mL) and CH2Cl2 (3×20 mL). The titled compound was isolated as a yellow solid (940 mg, 1.76 mmol, 56% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. washrinsing with H2O (2×20 mL) and CH2Cl2 (3×20 mL)

Sources & evidence

ORD record
ord-6098dcf605164d5f83530f4a5dc29b48
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…