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Diisopropylethylamine → HCID 58504086, compound

HRID 2407781
Notes
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Reaction equation

HRID 2407781 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:19])[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[S:27][C:28]([CH:31]=O)=[CH:29][N:30]=1.C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CN(C)C=O.C(OCC)(=O)C>[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:19])[CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:31][C:28]2[S:27][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[N:30][CH:29]=2)[CH2:17][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 534037722-(Pyridin-2-yl)-1,3-thiazole-5-carbaldehydeHCID 66989940HCID 66989940, compound

Product 1

HCID 58504086HCID 58504086, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 11
1,2-Dichloroethane
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the compound prepared in Example 308 (323 mg) and the compound prepared in Example 139 (267 mg) in 1,2-dichloroethane (10 mL) and N,N-dimethylformamide (4 mL) was added diisopropylethylamine (0.89 mL) and sodium triacetoxyborohydride (813 mg). The reaction mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 50-75% ethyl acetate/hexane) to furnish the title compound (222 mg) with the following physical properties.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 50-75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-141ad9dea7734435978b38ee1e905fa0
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes