Diisopropylethylamine → HCID 10099269, compound

HRID 1986659Notes

Reaction equation

HRID 1986659 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[NH2:23])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:32]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(N(C(C)C)CC)(C)C>CCN(CC)CC>[C:1]([C:5]1[CH:6]=[C:7]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[NH:23][C:38]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:39])=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 10366179HCID 10366179, compound

Product 1

HCID 10099269HCID 10099269, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 7-amino-1-methylindole-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (64 mg, 0.14 mmol), morpholinecarbonyl chloride (0.13 mL, 1.1 mmol), diisopropylethylamine (0.2 mL) and Et3N (0.5 mL) was stirred for 4 days. The reaction mixture was extracted and purified by reverse phase HPLC on a C18 column eluting with an acetonitrile-water gradient to provide 15 mg (19%) of the title compound.

Workup

  1. extractionThe reaction mixture was extracted
  2. custompurified by reverse phase HPLC on a C18 column
  3. washeluting with an acetonitrile-water gradient

Sources & evidence

ORD record
ord-bf5345919359470b81029bbea45245a2
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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