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Diisopropylethylamine → Ammonia

HRID 43403
Notes
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Reaction equation

HRID 43403 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:18][CH2:17][NH:16][C@@H:15]([CH3:19])[CH2:14]1)(=[O:12])=[O:11])[C:5]#[N:6].[CH3:20][C:21]1[N:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CO.C(Cl)Cl>[NH3:6].[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:27]([C:24]2[CH:25]=[N:26][C:21]([CH3:20])=[CH:22][CH:23]=2)=[O:28])[C@@H:15]([CH3:19])[CH2:14]1)(=[O:12])=[O:11])[C:5]#[N:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591520673-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

Product 2

HCID 222Ammonia
HCID 59161349
3-Methyl-4-({(3S)-3-methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-piperazinyl}sulfonyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (Description 11) (75 mg, 0.268 mmol), 6-methyl-3-pyridinecarboxylic acid (40.5 mg, 0.295 mmol) and DIPEA (0.070 ml, 0.403 mmol) in dry DMF (3 ml) at room temperature under Ar was added HATU (122 mg, 0.322 mmol) and the resulting yellow solution stirred at room temperature for 1 h. Concentration in vacuo gave a yellow oil, that was purified by MDAP purification; concentration of the desired fractions gave a clear film (78.8 mg). Flash chromatography (silica; Flash 12S; linear gradient (1-8%) [2M NH3 in MeOH] in DCM) gave the title compound as a clear film (54.5 mg) that became a white solid on standing in vacuo (1 mbar) for 1 hour.

Workup

  1. concentrationConcentration in vacuo
  2. customgave a yellow oil, that
  3. customwas purified by MDAP purification
  4. customconcentration of the desired fractions gave a clear film (78.8 mg)

Sources & evidence

ORD record
ord-136edae82d064d8f87bcad27fb7aff8f
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes