1-Pyrrolidineethanamine → 5-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamide

HRID 1372399Notes

Reaction equation

[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[CH3:12])=[O:2].[NH2:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>>[N:16]1([CH2:15][CH2:14][NH:13][C:9]([C:5]2[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=2[CH3:8])=[O:11])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Reactant 2

HCID 13441-Pyrrolidineethanamine

HCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 207617295-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamideYield 73%

Procedure

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (0.5 g, 2.99 mmol) was reacted with 1-(2-aminoethyl)pyrrolidine (0.42 mL) to give 0.57 g (73% yield) of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide using General Amidation Procedure 1. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.79 (br s, 1H, NH), 9.53 (s, 1H, CHO), 7.41 (m, 1H, NH), 3.28–3.34 (m, 2H, CH2), 2.53–2.60 (m, 6H, CH2 and 2×CH2), 2.35 (s, 3H, CH3), 2.3 (s, 3H, CH3), 1.68 (m, 4H, 2×CH2). MS m/z 264 [M+1].

Sources & evidence

ORD record: ord-94d0a839ac7d41bc9ef937cb09a22a34
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157577B2

Reaction notes

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