Diisopropylethylamine → 2-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

HRID 1025474

Reaction equation

HRID 1025474 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:26][CH2:25][CH2:24][CH2:23][C:5]=2[C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:8].[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](O)=[O:40])(=[O:35])=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39]([NH:1][C:2]2[S:3][C:4]3[CH2:26][CH2:25][CH2:24][CH2:23][C:5]=3[C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)=[O:8])=[O:40])(=[O:35])=[O:34])[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2574763-(Morpholine-4-sulfonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682078332-amino-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

Product 1

HCID 712384872-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamideYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 9.1 mg of 2-amino-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 8.1 mg of 3-(morpholine-4-sulfonyl)benzoic acid, 0.016 mL of N,N-diisopropylethylamine, and 0.5 mL of DMF was added a mixture of 11.4 mg of HATU and 0.1 mL of DMF, followed by stirring at 60° C. overnight. The reaction mixture was separated by the addition of chloroform and water, and then the organic layer was concentrated under reduced pressure. The obtained residue was purified by preparative high performance liquid chromatography (methanol-0.1% aqueous formic acid solution) to obtain 8.9 mg of 2-{[3-(morpholin-4-ylsulfonyl)benzoyl]amino}-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.

Workup

  1. additionwas added
  2. customThe reaction mixture was separated by the addition of chloroform and water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by preparative high performance liquid chromatography (methanol-0.1% aqueous formic acid solution)

Sources & evidence

ORD record
ord-fe82e848ec974b0d86516fe30451cd60
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Linked notes

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