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Diisopropylethylamine → HCID 178428249, compound

HRID 1091815
Notes
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Reaction equation

HRID 1091815 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])=[CH:18][CH:17]=3)[N:9]=2)[NH:4][N:3]=1.Cl.[CH:31]1([C:34]2([OH:38])[CH2:37][NH:36][CH2:35]2)[CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C>CCCCO.CCOC(C)=O>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8]2[CH:13]=[C:12]([N:36]3[CH2:37][C:34]([CH:31]4[CH2:33][CH2:32]4)([OH:38])[CH2:35]3)[N:11]=[C:10]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])=[CH:18][CH:17]=3)[N:9]=2)[NH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 467351503-Cyclopropylazetidin-3-ol hydrochlorideHCID 178428224HCID 178428224, compound

Product 1

HCID 178428249HCID 178428249, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
100 °C

Procedure

To a suspension of N-(4-(4-(3-methyl-1H-pyrazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)cyclopentanecarboxamide (200 mg, 0.47 mmol) and 3-cyclopropyl azetidin-3-ol hydrochloride (70 mg, 0.47 mmol) in n-BuOH (5 ml) was added diisopropylethylamine (239 mg, 1.88 mmol, 0.30 ml). The mixture was heated to 100° C. for 16 hrs and then allowed to cool to room temperature and diluted with EtOAc (30 ml) and sat NaHCO-3. The organic layer was washed with brine, dried (Na2SO4) and concentrated. Crude product was then purified by flash chromatography EtOAc 5% MeOH:EtOAc to give title compound as an off white solid (70 mg, 30%). 1H NMR (DMSO-d6) 0.30-0.35 (2H, m), 0.39-0.44 (2H, m), 1.16-1.21 (1H, m), 1.56-1.75 (6H, m), 1.83-1.90 (2H, m), 2.00 (3H, s), 2.76-2.82 (1H, m), 3.65 (4H, dd), 5.35 (1H, s), 5.58 (1H, s), 7.47 (2H, d), 7.72 (2H, d), 9.19 (1H, s), 10.06 (1H, s), 11.65 (1H, s). ES+ 506.

Workup

  1. temperatureto cool to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customCrude product was then purified by flash chromatography EtOAc 5% MeOH

Sources & evidence

ORD record
ord-3ec0cd7af6af42b095c4a8b3084f50af
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129399B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes