Pyrrole-2-Carboxylic Acid → HCID 51210632, compound

HRID 2238280Notes

Reaction equation

HRID 2238280 reaction equation
C(OC1C=CC(N)=CC=1)C1C=CC=CC=1.N1C=CC=C1C(O)=O.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([C:41]2[CH:46]=[CH:45][CH:44]=C[N:42]=2)=[O:40])=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:31][C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:39]([C:41]2[NH:42][CH:44]=[CH:45][CH:46]=2)=[O:40])=[CH:36][CH:37]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 12473Pyrrole-2-Carboxylic AcidHCID 228604-BenzyloxyanilineHCID 2425421N-[4-(benzyloxy)phenyl]pyridine-2-carboxamide

Product 1

HCID 51210632HCID 51210632, compound

Procedure

This compound was prepared from 4-benzyloxyaniline (4.0 g, 17 mmol) and pyrrole-2-carboxylic acid (1.98 g, 17.8 mmol), using the same method used to prepare pyridine-2-carboxylic acid (4-benzyloxyphenyl)amide. The product was purified by flash chromatography, on silica gel, using 5% methanol in DCM as the eluant, to give the product as a colorless solid, 2.6 g (50%). MS m/z 293 (MH+). 1H NMR(DMSO-d6) δ 5.04 (s, 2H), 6.13 (m, 1H), 6.95-7.05 (m, 4H), 7.28-7.45 (m, 5H), 7.65 (d, 2H), 9.7 (s, 1H) and 11.65 (s, 1H).

Workup

  1. customThe product was purified by flash chromatography, on silica gel

Sources & evidence

ORD record
ord-e2b448b4c30c432085fec9c3580bff8d
Source dataset
uspto-grants-2010_05
Patent number
US07718692B2

Reaction notes

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