1,1'-Carbonyldiimidazole → HCID 178488548, compound

HRID 82752Notes

Reaction equation

HRID 82752 reaction equation
[NH:1]1[C:5]([CH2:6][CH2:7][C:8]2[N:9]([C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][C:22]=3[CH3:30])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)=[N:4][N:3]=[N:2]1.C1N=C[N:33](C(N2C=NC=C2)=O)C=1.O.[NH4+]>C1COCC1>[NH:4]1[C:5]([CH2:6][CH2:7][C:8]2[N:9]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH2:33])=[O:26])=[CH:23][C:22]=3[CH3:30])[C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:11][CH:12]=2)=[N:1][N:2]=[N:3]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 22024077Azanium;hydrateHCID 1784885494-(2-(2-(1H-tetrazol-5-yl)ethyl)-5-(4-methoxyphenyl)-1H-pyrrol-1-yl)-3-methylbenzoic acid

Product 1

HCID 178488548HCID 178488548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-(2-(1H-tetrazol-5-yl)ethyl)-5-(4-methoxyphenyl)-1H-pyrrol-1-yl)-3-methylbenzoic acid (130 mg, 0.332 mmol) was dissolved in anhydrous THF (3 mL). CDI (68 mg, 0.419 mmol) was added in three portions at room temperature and stirred at this temperature for 1 h. The resultant yellow solution was added dropwise to 25% ammonium hydrate (3 mL) at 0° C. After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was evaporated in vacuo and the residue was purified by prep-HPLC to afford 2H, R2=4-methoxyphenyl as a yellow solid (7 mg, 5.4%).

Workup

  1. additionAfter the addition
  2. stirringstirred for 2 h
  3. customThe mixture was evaporated in vacuo
  4. customthe residue was purified by prep-HPLC
  5. customto afford 2H

Sources & evidence

ORD record
ord-8b0e96c9bf7748d48863ccca7c98cf26
Source dataset
uspto-grants-2014_09
Patent number
US08846736B2

Reaction notes

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