Triethylamine → HCID 44469673, compound

HRID 2175450Notes

Reaction equation

HRID 2175450 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 offwhite solid. 1H-NMR (CDC3, 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-1dbc28e6f9654effbd10c2b6e1b0a2c3
Source dataset
uspto-grants-2015_06
Patent number
US09062052B2

Reaction notes

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