Triethylamine → HCID 67322638, compound

HRID 1846650Notes

Reaction equation

HRID 1846650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[C:9]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([OH:29])=O)[CH2:22][CH2:21]2)=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)=[O:6].[CH3:33][N:34]1[CH2:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[C:9]([N:20]2[CH2:21][CH2:22][CH:23]([CH2:26][C:27]([N:37]3[CH2:38][CH2:39][CH2:40][N:34]([CH3:33])[CH2:35][CH2:36]3)=[O:29])[CH2:24][CH2:25]2)=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2283491-MethylhomopiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68304426HCID 68304426, compound

Product 1

HCID 67322638HCID 67322638, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.035 g (0.078 mmol) of [3′-(3-chloro-benzoylamino)-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid, 0.044 g (0.39 mmol) of 1-methyl homopiperazine, 0.032 g (0.10 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, and 0.032 mL (0.23 mmol) of triethylamine in N,N-dimethylformamide (2 mL) are stirred overnight at room temperature. The mixture is concentrated under reduced pressure and the residue is diluted with water which causes a solid to precipitate from solution. The colorless solid is collected by filtration, washed with water and dried to provide 0.032 g (75%) of 3-chloro-N-(2-{4-[2-(4-methyl-1,4-diazepan-1-yl)-2-oxoethyl]piperidin-1-yl}-5-phenylpyridin-3-yl)benzamide (124) as a colorless solid. [M+H]+=546.3.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionthe residue is diluted with water which
  3. customto precipitate from solution
  4. filtrationThe colorless solid is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e0b8a9d42c37473fa25b665d7c78d290
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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