1,1'-Carbonyldiimidazole → HCID 178488548, compound

HRID 1261412Notes

Reaction equation

HRID 1261412 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-c79a4adc69b741fdae7ecd93ebed744a
Source dataset
uspto-grants-2013_06
Patent number
US08470857B2

Reaction notes

Loading…