Sodium hydride → HCID 69433406, compound

HRID 1593436Notes

Reaction equation

HRID 1593436 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:10]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[CH2:23][CH2:22]4)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[N:16]1[CH:15]=[CH:14][C:13]([C:11]2[O:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:7][CH:6]=3)=[CH:9][C:10]=2[C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[CH2:23][CH2:22]3)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 516892Sodium BicarbonateHCID 136334111HCID 136334111, compound

Product 1

HCID 69433406HCID 69433406, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from Step 5 (0.18 g, 0.47 mmol) in dimethylformamide (3 ml) was treated at 0° C. with sodium hydride (0.021 g of a 60% suspension in mineral oil, 0.52 mmol). The reaction mixture was stirred at 0° C. for 10 minutes and treated with another portion of sodium hydride (0.021 g of a 60% suspension in mineral oil, 0.52 mmol) and 1-(2-chloroethyl)pyrrolidine hydrochloride salt (0.088 g, 0.52 mmol) and stirred at room temperature overnight. The reaction mixture was poured onto aqueous sodium bicarbonate solution and the mixture was applied to an SCX column eluting with methanol followed by a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95) to afford the title compound (0.081 mg, 36%); MS(ES+) m/e 465 [M+H]+.

Workup

  1. stirringstirred at room temperature overnight
  2. washeluting with methanol
  3. additionfollowed by a mixture of 0.880 ammonia/methanol (1:9)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95)

Sources & evidence

ORD record
ord-1daa1ff797d9474ca17e95d746fae435
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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