1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67446410, compound

HRID 1667237Notes

Reaction equation

[OH:1][NH:2]/[C:3](=[N:15]\[H])/[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.[O:17]=[C:18]1[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][N:19]1[CH2:36][C:37](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[C:30]1([C:23]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][CH2:21][CH2:20][N:19]([CH2:36][C:37]3[O:1][N:2]=[C:3]([C:4]4[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=4)[N:15]=3)[C:18]2=[O:17])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(Z)—N-Hydroxy-4-(trifluoromethoxy)benzimidamide (0.125 g, 0.566 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.175 g, 0.566 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.163 g, 0.849 mmol) were stirred together in dichloroethane (4 mL) at room temperature for 45 minutes, then heated to 85° C. and stirred for 16 hours. The reaction was cooled and concentrated. Silica gel chromatography using a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) eluting with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes gave the title compound. 1H NMR (300 MHz, CDCl3) δ 8.22-8.08 (m, 2H), 7.43-7.16 (m, 12H), 4.92 (s, 2H), 3.62 (t, J=6.5, 2H), 2.80-2.61 (m, 2H), 2.03-1.80 (m, 2H); MS (ESI+) m/z 494.1 (M+H)+.

Workup

temperatureThe reaction was cooled
concentrationconcentrated
washeluting with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (Flow=35 mL/minute) over 30 minutes

Sources & evidence

ORD record: ord-f32dcdcb9c944d56a0618f46902036fb
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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