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1,2-Dichloroethane → HCID 69932959, compound

HRID 540796
Notes
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Reaction equation

HRID 540796 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:36]=[CH:35][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14](O)=[O:15])[N:11]=[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][O:25][CH2:24]4)[CH:18]=3)[CH:9]=2)=[CH:5][CH:4]=1.Cl.[CH3:40][NH:41][CH3:42].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:36]=[CH:35][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14]([N:41]([CH3:42])[CH3:40])=[O:15])[N:11]=[C:10]([C:17]3[CH:18]=[C:19]([C:23]4([NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:24][O:25][CH2:26]4)[CH:20]=[CH:21][CH:22]=3)[CH:9]=2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67111333HCID 67111333, compound

Product 1

HCID 69932959HCID 69932959, compound

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5-(4-Trifluoromethylphenoxy)-3-(3-{3-[(tert-butyloxycarbonyl)amino]oxetan-3-yl}phenyl)-1H-pyrazol-1-yl]acetic acid (85 mg, 0.16 mmol), dimethylamine hydrochloride (26 mg, 0.32 mmol), EDC (46 mg, 0.24 mmol), HOBT (37 mg, 0.24 mmol), and diisopropylethylamine (0.11 mL, 0.64 mmol) were combined in 0.5 mL of DMF and the mixture was stirred at ambient temperature for 18 h. The mixture was diluted with EtOAc and washed with water and brine. The organic phase was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was chromatographed on a 12 g silica gel column using 0-5% MeOH:CHCl3 over 15 min at 30 mL/min. Product-containing fractions were combined and the solvents were evaporated under reduced pressure to give tert-butyl [3-(3-{5-(4-trifluoromethylphenoxy)-1-[2-(dimethylamino)-2-oxoethyl]-1H-pyrazol-3-yl}phenyl)oxetan-3-yl]carbamate as a foam. Calcd (M+1)+: 561.6. Found: 561.0

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed on a 12 g silica gel column
  6. waitCHCl3 over 15 min at 30 mL/min
  7. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-d754bcbfaf3e4cd4be3c72fcc25763ce
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes