1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67376344, compound

HRID 1667218Notes

Reaction equation

[OH:1][NH:2]/[C:3](=[N:14]\[H])/[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.[O:16]=[C:17]1[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][N:18]1[CH2:35][C:36](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[C:29]1([C:22]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:21][CH2:20][CH2:19][N:18]([CH2:35][C:36]3[O:1][N:2]=[C:3]([C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=4)[N:14]=3)[C:17]2=[O:16])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of (Z)—N-hydroxy-3-(trifluoromethyl)benzimidamide (0.155 g, 0.761 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.214 g, 0.692 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.172 g, 0.899 mmol) were stirred together in dichloroethane (0.5 mL) at room temperature for 3 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF15-12 column (Analogix®) and the product eluted using a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate over 30 minutes (Flow=30 mL/minute) to supply the title compound. 1H NMR (300 MHz, CDCl3) δ 8.40 (s, 1H), 8.31 (d, J=7.7, 1H), 7.80 (d, J=7.9, 1H), 7.64 (dd, J=6.4, 14.3, 1H), 7.39-7.10 (m, 10H), 4.89 (d, J=20.0, 2H), 3.70-3.56 (m, 2H), 2.70 (dt, J=11.5, 25.9, 2H), 1.92 (dtd, J=3.1, 6.4, 9.4, 2H).

Workup

temperatureThe reaction was cooled
washthe product eluted
customover 30 minutes

Sources & evidence

ORD record: ord-e3b8f3b78bd44c679c927338c025d9ce
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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