Triethylamine → HCID 178431605, compound

HRID 2367758Notes

Reaction equation

HRID 2367758 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.CCN(CC)CC.[CH3:43][C:44]1([CH3:51])[O:49][CH2:48][C:47](=O)[CH2:46][O:45]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:21][CH2:22][N:23]([CH:47]4[CH2:48][O:49][C:44]([CH3:51])([CH3:43])[O:45][CH2:46]4)[CH2:24][CH2:25]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5049666Sodium triacetoxyborohydrideHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Product 1

HCID 178431605HCID 178431605, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (81 mg, 0.16 mmol, as prepared in Example 14, step (b)) in CH2Cl2 (3 mL) was added NEt3 (33 μL, 0.24 mmol). The solution was then treated with 2,2-dimethyl-[1,3]dioxan-5-one (31 mg, 0.24 mmol) and the reaction was allowed to stir for 3 h. At this time NaBH(OAc)3 (51 mg, 0.24 mmol) was added in one portion, and the reaction was allowed to stir for an additional 4 h. The reaction was diluted with H2O (10 mL) and extracted with EtOAc (2×25 mL). The organic extracts were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel preparative thin layer chromatography (10% MeOH—CHCl3) afforded 22 mg (28%) of the title compound as an off-white semi-solid. Mass spectrum (ESI, m/z): Calcd. for C28H35N5O3, 490.2 (M+H). found 490.6.

Workup

  1. stirringto stir for an additional 4 h
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel preparative thin layer chromatography (10% MeOH—CHCl3)

Sources & evidence

ORD record
ord-a7fa6d1c77c04f6585582f5c46aa81bc
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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