Water → HCID 67779655, compound

HRID 356171Notes

Reaction equation

HRID 356171 reaction equation
[C:1]1(=[O:29])[N:5]([CH2:6][C:7]([N:9]2[C@@H:15]3[CH2:16][CH2:17][CH2:18][C@@H:14]3[C:13](=[O:19])[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.[H-].[Na+].Cl[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.O>CN(C)C=O>[C:4]1(=[O:24])[N:5]([CH2:6][C:7]([N:9]2[C@@H:15]3[CH2:16][CH2:17][CH2:18][C@@H:14]3[C:13](=[O:19])[N:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])[C:1](=[O:29])[C:2]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:3]12

Participants

6

Reactant 4

HCID 962WaterHCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 70111957HCID 70111957, compound

Product 1

HCID 67779655HCID 67779655, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In a mixture of water (0.5 mL) and ethyl acetate (1 mL)was dissolved 2-(chloromethyl)pyridine hydrochloride (246 mg, 1.5 mmol). This solution was neutralized with the addition of sodium hydrogencarbonate. The organic layer was separated, and the remaining aqueous layer was subjected to extraction twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate, followed by concentration under reduced pressure to give 2-(chloromethyl)pyridine. To a suspension of (3aR*,10aS*)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (389 mg, 1.0 mmol) in N,N-dimethylformamide (3 mL), which was cooled to 0° C., was added sodium hydride (60% liquid paraffin dispersion, 44 mg, 1.1 mmol). The mixture was stirred for 3 minutes at the same temperature and for 10 minutes at room temperature. To this mixture was added a solution of the 2-(chloromethyl)pyridine, which was produce by the above-mentioned procedure, in N,N-dimethylformamide (0.5 mL). The mixture was stirred for 3 hours at room temperature. To the reaction mixture was added water, and resulting precipitate was collected by filtration, which was recrystallized from chloroform-ethanol-diisopropylether to give 232 mg (yield 48%) of the titled compound, m.p. 227°-229° C.

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. customresulting precipitate
  3. filtrationwas collected by filtration, which
  4. customwas recrystallized from chloroform-ethanol-diisopropylether

Sources & evidence

ORD record
ord-298945b72b954dfd956faf49484fdabb
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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