Triethylamine → HCID 44469673, compound

HRID 1626347Notes

Reaction equation

HRID 1626347 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CN(C(ON1N=N[C:45]2[CH:46]=[CH:47][CH:48]=[N:49][C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:59]([O:61][C:62]1[CH:74]=[CH:73][C:65]([CH2:66]C2CCNCC2)=[CH:64][CH:63]=1)[CH3:60]>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([C:21]([CH:46]4[CH2:45][CH2:44][N:49]([CH2:66][C:65]5[CH:73]=[CH:74][C:62]([O:61][CH2:59][CH3:60])=[CH:63][CH:64]=5)[CH2:48][CH2:47]4)=[O:23])=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[CH:26][CH:27]=1)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 47782654-(4-ethoxybenzyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69008872HCID 69008872, compound

Product 1

HCID 44469673HCID 44469673, compoundYield 450.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoic acid (100 mg, 0.275 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added triethylamine (84 μl, 0.825 mmol), HATU (115 mg, 0.3 mmol), and 4-(4-ethoxybenzyl)piperidine (61 mg, 0.275 mmol). The mixture was stirred at room temperature overnight and then poured into water. The resulting solids were collected by filtration, purified by column chromatography to yield 0.7 g (55%) of N-(1-(4-cyanobenzyl)piperidin-4-yl)-4-(1-(4-ethoxybenzyl)piperidine-4-carbonyl)benzamide (compound 27) as an off white solid. 1H-NMR (CDCl3, 300 MHz): δ 7.761 (d, 2H), 7.600 (m, 2H), 7.434 (m, 4H), 7.022 (d, 2H), 6.812 (d, 2H), 6.022 (d, 1H), 4.658 (m, 1H), 3.994 (dd, 2H), 3.569 (m, 3H), 2.885 (m, 4H), 2.505 (m, 2H), 2.227 (m, 2H), 2.049 (m, 2H), 1.639 (m, 6H), 1.405 (m, 3H); LCMS (m/z): 565 (MH+).

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-d9733cebe27e45028df77ff9a49b2534
Source dataset
uspto-grants-2014_07
Patent number
US08785449B2

Reaction notes

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