Water → Acetamide, N-[8-(4-cyano-1-naphthalenyl)-8-azabicyclo[3.2.1]oct-3-yl]-

HRID 916352Notes

Reaction equation

HRID 916352 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[NH2:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]#[N:26])=[CH:17][CH:16]=3)[CH:9]([CH2:10][CH2:11]2)[CH2:8]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[C:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([N:14]2[CH:12]3[CH2:11][CH2:10][CH:9]2[CH2:8][CH:7]([NH:6][C:1](=[O:3])[CH3:2])[CH2:13]3)=[CH:16][CH:17]=1)#[N:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 1317266004-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

Product 1

HCID 11493459Acetamide, N-[8-(4-cyano-1-naphthalenyl)-8-azabicyclo[3.2.1]oct-3-yl]-Yield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a −30° C. solution of acetyl chloride (15 μL, 0.21 mmol) in DMF (1.5 mL) was added dropwise a solution of 165RL21 (54 mg, 0.20 mmol) and DIPEA (37 μL, 0.21 mmol) in DMF (3.5 mL). After 1 hour of stirring the reaction mixture was brought to rt and allowed to react overnight. Water (20 mL) was then added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel using ethyl acetate/MeOH (9:1) to give the desired compound (35 mg, 56%).

Workup

  1. customwas brought to rt
  2. customto react overnight
  3. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f9398516809e4f2fb3a36df8c11e131f
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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