Diisopropylethylamine → HCID 76774448, compound

HRID 1970188Notes

Reaction equation

HRID 1970188 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([N:13]([C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[C:39]([F:42])([F:41])[F:40])[N:26]=[CH:25]4)[C:18](=[O:20])[N:19]=2)[CH3:14])[CH2:10][CH:9]1[C:43](O)=[O:44])=O)(C)(C)C.Cl.[CH3:47][O:48][NH2:49].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:47][O:48][NH:49][C:43]([CH:9]1[CH2:10][CH:11]([N:13]([C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[C:39]([F:41])([F:40])[F:42])[N:26]=[CH:25]4)[C:18](=[O:20])[N:19]=2)[CH3:14])[CH2:12][NH:8]1)=[O:44]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67346871HCID 67346871, compound

Product 1

HCID 76774448HCID 76774448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-({5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-4-oxo-4,5-dihydro-thiazol-2-yl}-methyl-amino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.066 g, 0.1 mmol) and methoxyamine hydrochloride (0.014 g, 0.15 mmol) in DMF (2 mL) was added EDC hydrochloride (0.03 g, 0.15 mmol) followed by DIPEA (0.3 mL, 1.72 mml). The reaction mixture was stirred at room temperature for 16 hours and partitioned between water and dichloromethane. The dichloromethane layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (100% ethyl acetate) to yield the title compound.

Workup

  1. custompartitioned between water and dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-46f13a30bc86466a962cbf61b796fcf1
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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