2,6-Dimethylbenzoic acid → HCID 68970441, compound

HRID 1726257Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13]2)[CH2:8][CH2:7]1)[CH3:5].[CH3:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:31]=1[C:32](O)=[O:33]>>[C:25]([C:24]1[CH:23]=[CH:22][C:21]([C:12]2([CH:9]3[CH2:10][CH2:11][N:6]([CH:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:32](=[O:33])[C:31]4[C:35]([CH3:39])=[CH:36][CH:37]=[CH:38][C:30]=4[CH3:29])[CH2:7][CH2:8]3)[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13]2)=[CH:28][CH:27]=1)#[N:26]

Participants

Reactant 2

HCID 124392,6-Dimethylbenzoic acid

HCID 68970718HCID 68970718, compound

Product 1

HCID 68970441HCID 68970441, compoundYield 75%

Procedure

Using general procedure E, 4-{2-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-benzo[1,3]dioxol-2-yl}-benzonitrile (see EXAMPLE 277) (64 mg, 0.17 mmol) and 2,6-dimethylbenzoic acid (28 mg, 0.19 mmol) afforded COMPOUND 279 as a white foam (65 mg, 75%). 1H NMR (CDCl3) δ0.93 (d, 3H, J=6.6 Hz), 0.94-1.23 (m, 2H), 1.42-1.58 (m, 3H), 1.65-1.78 (m, 1H), 1.86-1.98 (m, 2H), 2.28-2.36 (m, 1H), 2.31 (s, 6H), 2.68-2.79 (m, 3H), 3.26-3.36 (m, 1H), 3.71-3.82 (m, 1H), 6.76-6.80 (m, 4H), 7.03 (d, 2H, J=7.8 Hz), 7.15-7.20 (m, 1H), 7.43 (br s, 1H), 7.51-7.53 (m, 2H), 7.61-7.64 (m, 2H). ES-MS m/z 510 (M+H).

Sources & evidence

ORD record: ord-7021a6537b1e4ed79ddce4960e172f1c
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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