Acetic Acid → HCID 178476304, compound

HRID 1508020Notes

Reaction equation

HRID 1508020 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[NH:17][CH:18]=[C:19]([C:21]#[N:22])[N:20]=2)=[O:15])=[C:9]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)[CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].[C:29]([OH:32])(=[O:31])[CH3:30]>C1COCC1.[Zn]>[C:29]([OH:32])(=[O:31])[CH3:30].[NH2:1][C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[NH:17][CH:18]=[C:19]([C:21]#[N:22])[N:20]=2)=[O:15])=[C:9]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)[CH:8]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1784580634-Cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Product 1

HCID 178476304HCID 178476304, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide (as prepared in the previous step, 13.6 mg, 0.0362 mmol) and zinc (9.5 mg, 0.15 mmol) in 1 mL of THF was added acetic acid (0.20 mL). The resulting mixture was stirred at RT for 3 h under Ar. The solid was removed by filtration on Celite and the filtrate was concentrated in vacuo to give a light brown oil. The mixture was triturated with DCM (2×4 mL). The solvent was removed by filtration and the solid was dried in vacuo to give 13.5 mg (91%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.27 (s, 1H), 7.70 (s, 1H), 7.43 (d, 1H, J=7.3 Hz), 7.29 (s, 1H), 5.81 (m, 1H), 2.11-2.37 (m, 4H), 1.91 (s, 3H), 1.59-1.84 (m, 4H), 1.71 (s, 6H).

Workup

  1. customThe solid was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a light brown oil
  4. customThe mixture was triturated with DCM (2×4 mL)
  5. customThe solvent was removed by filtration
  6. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-3eaa246070a24605a7684e2384e7c9e6
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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