Acetic Acid → HCID 178473833, compound

HRID 536928Notes

Reaction equation

HRID 536928 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=3)=[O:21])=[C:15]([C:29]3[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31][CH:30]=3)[CH:14]=2)([N:10]=[N+]=[N-])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:37]([OH:40])(=[O:39])[CH3:38]>C1COCC1.[Zn]>[C:37]([OH:40])(=[O:39])[CH3:38].[C:1]([N:4]1[CH2:5][CH2:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=3)=[O:21])=[C:15]([C:29]3[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31][CH:30]=3)[CH:14]=2)([NH2:10])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178473857HCID 178473857, compound

Product 1

HCID 178473833HCID 178473833, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [4-(1-acetyl-4-azido-piperidin-4-yl)-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 40.0 mg, 0.0822 mmol) and zinc (54.0 mg, 0.822 mmol) in 1.6 mL of THF was added acetic acid (0.40 mL). The resulting mixture was stirred at RT for 16 h under Ar. The solid was removed by filtration on Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (10% MeOH/DCM) to give 13 mg (30%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.33 (d, 1H, J=8.6 Hz), 7.91 (s, 1H), 7.52 (dd, 1H, J=8.6, 2.3 Hz), 7.40 (s, 1H), 5.77 (m, 1H), 3.76-3.98 (m, 2H), 3.42 (m, 2H), 2.46 (m, 2H), 2.32 (m, 2H), 2.13 (s, 3H), 2.07 (m, 2H), 1.86-2.03 (m, 2H), 1.93 (s, 6H), 1.59 (t, 2H, J=6.1 Hz). Mass spectrum (ESI-neg, m/z): Calcd. for C26H32N6O2, 459.3 (M−H). found 459.5.

Workup

  1. customThe solid was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (10% MeOH/DCM)

Sources & evidence

ORD record
ord-98c99ae153584f98b738f14ba4160d64
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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