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Diisopropylethylamine → HCID 66990601, compound

HRID 2407730
Notes
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Reaction equation

HRID 2407730 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[C:11]([CH3:17])[C:10]=1[C:18]#[N:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[S:27][C:28]([CH2:31][N:32]2[CH2:37][CH2:36][CH:35]([CH2:38]O)[CH2:34][CH2:33]2)=[CH:29][N:30]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([O:16][CH2:38][CH:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:28]3[S:27][C:26]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=4)=[N:30][CH:29]=3)[CH2:33][CH2:34]2)=[O:15])=[C:11]([CH3:17])[C:10]=1[C:18]#[N:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58504208HCID 58504208, compoundHCID 66990613HCID 66990613, compound

Product 1

HCID 66990601
HCID 66990601, compound
Yield 25%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

The compound prepared in Example 222 (0.100 g), the compound prepared in Example 220 (0.123 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.102 g), N,N-diisopropylethylamine (0.185 mL) and 4-dimethylaminopyridine (0.011 g) were suspended in N,N-dimethylacetamide (10 mL) and heated at 60° C. overnight. The reaction mixture was cooled to room temperature and suspended between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 25 to 50% ethyl acetate/hexane/1% (9:1 methanol/concentrated ammonium hydroxide) to furnish the title compound (0.049 g) with the following physical properties.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude material, which
  7. customwas purified by flash column chromatography (eluant

Sources & evidence

ORD record
ord-3eed46efe18144e69fa973c379b6256f
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes