Triethylamine → 3-(Adamantan-1-yloxymethyl)-1-o-tolyl-1H-pyrazole-4-carboxylic acid benzyl ester

HRID 967796Notes

Reaction equation

HRID 967796 reaction equation
CCN(CC)CC.[CH2:8]([O:15][C:16](=[O:36])[C:17]([C:22](=O)[CH2:23][O:24][C:25]12[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2)=[CH:18]N(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[C:38]1([CH3:46])[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[NH:44][NH2:45]>CC#N>[CH2:8]([O:15][C:16]([C:17]1[C:22]([CH2:23][O:24][C:25]23[CH2:26][CH:27]4[CH2:33][CH:31]([CH2:30][CH:29]([CH2:28]4)[CH2:34]2)[CH2:32]3)=[N:45][N:44]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[CH3:46])[CH:18]=1)=[O:36])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 697980742-[2-(Adamantan-1-yloxy)-acetyl]-3-dimethylamino-acrylic acid benzyl ester

Product 1

HCID 697984193-(Adamantan-1-yloxymethyl)-1-o-tolyl-1H-pyrazole-4-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NEt3 (0.2 mL, 1.43 mmol) was added to a mixture of 2-[2-(adamantan-1-yloxy)-acetyl]-3-dimethylamino-acrylic acid benzyl ester (0.539 g, 1.4 mmol), and o-tolylhydrazine hydrochloride (0.222 g, 1.4 mmol) in MeCN (8 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 17 h. The precipitated solid was filtered off, washed with MeCN and dried to afford the product, (0.359 g, 56%).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with MeCN
  3. customdried
  4. customto afford the product, (0.359 g, 56%)

Sources & evidence

ORD record
ord-795ea83b7fe1485f9d07855d326405d7
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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