1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274311, compound

HRID 1667270Notes

Reaction equation

[OH:1][NH:2]/[C:3](/[C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10][CH:11]=1)=[N:4]\[H].[O:20]=[C:21]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][N:22]1[CH2:38][C:39](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[O:20]=[C:21]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:23][N:22]1[CH2:38][C:39]1[O:1][N:2]=[C:3]([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10][CH:11]=2)[N:4]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of (Z)-tert-butyl 5-(N-hydroxycarbamimidoyl)pyridin-2-ylcarbamate (0.131 g, 0.5 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.153 g, 0.5 mmol; Example 1C) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.199 g, 1.0 mmol) were stirred together in dichloroethane (7.0 mL) at room temperature for 2 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF25-40 column (Analogix®) and the product eluted using a gradient of 10% ethyl acetate/hexanes to 70% ethyl acetate over 30 minutes (Flow=30 mL/minute) to supply the title compound.

Workup

temperatureThe reaction was cooled
washthe product eluted
customover 30 minutes

Sources & evidence

ORD record: ord-318683bc071c41a2a9c37aa385ea002c
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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