Diisopropylethylamine → 1-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid methyl ester

HRID 928366Notes

Reaction equation

HRID 928366 reaction equation
[N:1]1([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:15][O:16][C:17](=[O:25])/[C:18](/[N+:23]#[C-:24])=[CH:19]/N(C)C.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:15][O:16][C:17]([C:18]1[N:23]=[CH:24][N:12]([CH2:11][C:10]2[CH:13]=[CH:14][C:7]([CH2:6][N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)=[CH:8][CH:9]=2)[CH:19]=1)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2758506Methyl 3-(dimethylamino)-2-isocyanoacrylateHCID 7131579{4-[(1H-pyrazol-1-yl)methyl]phenyl}methanamine

Product 1

HCID 580813081-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-Pyrazol-1-ylmethyl-benzylamine (550 mg, 2.5 mmol), (Z)-methyl-3-(dimethylamino)-2-isocyanoacrylate (380 mg, 2.5 mmol) and DIPEA (1.3 mL, 7.4 mmol) in 20 mL nBuOH was heated to 120° C. for 16 h. The mixture was concentrated in vacuo and the crude product was used in the next step without further purification. LCMS (method A) RtA=1.210 min; [M+H]+=297.0.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude product was used in the next step without further purification
  3. customLCMS (method A) RtA=1.210 min

Sources & evidence

ORD record
ord-5b508a04cd734dd5b83b63da1e94f590
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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