HCID 12043292, compound → HCID 131723475, compound

HRID 1278571Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5]([C:19]([O:21][CH3:22])=[O:20])[CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH:24]1([N:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][NH2:39])[CH2:32][CH2:31]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:23][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:39][CH2:38][CH2:37][CH2:36][N:33]2[CH2:32][CH2:31][N:30]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:35][CH2:34]2)=[O:18])[C:5]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

Reactant 2

HCID 12043292HCID 12043292, compound

HCID 12968483HCID 12968483, compound

Product 1

HCID 131723475HCID 131723475, compound

Procedure

The compound of Example 4 and 4-(cyclohexyl)-1-piperazinepropanamine were reacted according to the General Procedure of Example 13 to yield 1,4-dihydro-2,6-dimethyl-4-[5-[[3-(4-cyclohexyl-1-piperazinyl) propyl]amino]-5-oxopentyl]-3,5-pyridine dicarboxylic acid, dimethyl ester. 1H NMR (DMSO-d6) δ 8.71 (s, 1 H), 8 7.70 (br. t, 1 H), 3.75 (t, 1 H, J=5.4 Hz), 3.59 (s, 6 H), 3.15 (m, 1 H), 2.99 (m, 2 H), 2.45 (m,4 H),2.15 (s,6 H), 1.94 (t, 2 H, J=7.3 Hz), 1.7 (m, 4 H), 1.4-1.2 (m, 9 H), 1.2-1.0 (m, 11 H); 13C NMR (DMSO-d6) δ 171.8, 167.6, 146.3, 100.5, 62.5, 55.6, 53.4, 50.5, 48.4, 44.8, 36.9, 36.5, 35.6, 34.0, 32.0, 28.4, 26.4, 25.9, 25.6, 18.1. Analysis calculated for C29H48N4O5. 2.0 H2O: C, 61.24; H, 9.22; N, 9.85. Found: C, 61.44; H, 9.30; N, 10.53.

Sources & evidence

ORD record: ord-0f0c4341f4c4426e919282f33c4665fa
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444675B2

Reaction notes

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