Triethylamine → HCID 44469817, compound

HRID 539839Notes

Reaction equation

HRID 539839 reaction equation
Cl.[C:2]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][C:13]([C:19](O)=[O:20])=[CH:14][CH:15]=3)[CH2:10]2)=[CH:6][CH:5]=1)#[N:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH2:50][CH:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][CH:59]=2)[CH2:53][CH2:52]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][C:13]([C:19]([NH:50][CH:51]4[CH2:56][CH2:55][N:54]([CH2:57][C:58]5[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][CH:59]=5)[CH2:53][CH2:52]4)=[O:20])=[CH:14][CH:15]=3)[CH2:10]2)=[CH:22][CH:23]=1)#[N:3]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44120478HCID 44120478, compoundHCID 66897349HCID 66897349, compound

Product 1

HCID 44469817HCID 44469817, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-cyanobenzyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid hydrochloride (50 mg, 0.17 mmol) in DMF (2 mL), HATU (78 mg, 0.21 mmol), 4-amino-1-(4-cyanobenzyl)piperidine dihydrochloride (52 mg, 0.18 mmol) and triethylamine (125 uL, 91 mg, 0.9 mmol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight and poured into saturated sodium bicarbonate solution (30 mL) to give a white precipitate which was filtered and dried under vacuum. The resulting solid was triturated with ethyl ether to provide 2-(4-cyanobenzyl)-N-(1-(4-cyanobenzyl)piperidin-4-yl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (compound 37) as a white crystalline solid (69 mg, 82%). 1H NMR (DMSO-d6): δ 8.08 (1H, d, J=7.7 Hz); 7.79 (4H, dd, J=8.5, 6.9 Hz); 7.60-7.54 (3H, m); 7.49 (3H, d, J=8.8 Hz); 7.16 (1H, d, J=8.3 Hz); 3.78-3.66 (3H, m); 3.55 (4H, br s); 2.86 (2H, t, J=5.2 Hz); 2.82-2.66 (4H, m); 2.04 (2H, t, J=11.3 Hz); 1.75 (2H, d, J=11.3 Hz); 1.55 (2H, q, J=11.8 Hz). MS (M+H)+=490.

Workup

  1. customThe resulting reaction mixture
  2. customto give a white precipitate which
  3. filtrationwas filtered
  4. customdried under vacuum
  5. customThe resulting solid was triturated with ethyl ether

Sources & evidence

ORD record
ord-667c0834e2d04293aef37d0875222e38
Source dataset
uspto-grants-2014_10
Patent number
US08871770B2

Reaction notes

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