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4-Methylmorpholine → HCID 44156014, compound

HRID 572627
Notes
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Reaction equation

HRID 572627 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14]([OH:16])=O)[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH3:56][N:57]1[C:61]([NH2:62])=[CH:60][C:59]([CH3:63])=[N:58]1>CN(C=O)C>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14]([NH:62][C:61]2[N:57]([CH3:56])[N:58]=[C:59]([CH3:63])[CH:60]=2)=[O:16])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441558954-Cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

Product 1

HCID 44156014HCID 44156014, compound
Yield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.030 g, 0.07 mmol), HBTU (0.080 g, 0.21 mmol), N-methyl morpholine (0.023 mL, 0.21 mmol) and DMF (1 mL) were added to a sealed reaction tube containing 1,3-dimethyl-1H-pyrazol-5-amine (0.023 g, 0.21 mmol). The reaction mixture was allowed to shake overnight and was concentrated. The residue was dissolved up in THF/chloroform (1:3) (4 mL) and washed with sat NaHCO3 (2 mL). The organic solution was separated and concentrated. The crude product was dissolved in DMSO (1.5 mL) and was purified by reverse phase chromatography to give 4-cyano-3-(3,4-dichlorophenyl)-N-(1,3-dimethyl-1H-pyrazol-5-yl)-5-morpholin-4-ylthiophene-2-carboxamide (85) (0.003 g, 10%). LCMS: (FA) ES+ 476.4.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved up in THF/chloroform (1:3) (4 mL)
  3. washwashed
  4. customThe organic solution was separated
  5. concentrationconcentrated
  6. dissolutionThe crude product was dissolved in DMSO (1.5 mL)
  7. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-c81ab7cfe17847249b094d835e7dfec1
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029411B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes