Isopropanol → HCID 46205769, compound

HRID 2366447Notes

Reaction equation

HRID 2366447 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(O)=[O:2].C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.Cl.[NH2:37][C:38]1[C:46]([NH2:47])=[CH:45][CH:44]=[CH:43][C:39]=1[C:40]([NH2:42])=[O:41].C(O)(C)C>N1C=CC=CC=1.CN(C=O)C>[NH2:37][C:38]1[C:39]([C:40](=[O:41])[NH2:42])=[CH:43][CH:44]=[CH:45][C:46]=1[NH:47][C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[O:2]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 46205769HCID 46205769, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 4-(4-carboxyphenyl)-piperidine-1-carboxylate (1 g) in pyridine (3 mL) and DMF (3 mL) at 40° C. was stirred for 30 minutes, treated with carbonyl diimidazole (CDI, 0.55 g), stirred for 1 hour, treated with 2,3-diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, 0.73 g), stirred for 1 hour at ambient temperature, treated with isopropanol, (10 mL), cooled for 18 hours at 0° C. and filtered. The filtrant was dissolved in water (10 mL), treated with 50% aqueous NaOH (0.26 mL), stirred for 3 hours at ambient temperature and filtered.

Workup

  1. customsynthesized
  2. stirring6,737,421, 0.73 g), stirred for 1 hour at ambient temperature
  3. filtrationfiltered
  4. dissolutionThe filtrant was dissolved in water (10 mL)
  5. additiontreated with 50% aqueous NaOH (0.26 mL)
  6. stirringstirred for 3 hours at ambient temperature
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d52ec5db8c674eac8e6618caa42358be
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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