4-Methylmorpholine → 5-Ethynyl-N-{3-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]-tetrahydrofuran-3-yl}thiophene-2-carboxamide

HRID 229346Notes

Reaction equation

HRID 229346 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)#[CH:2].[NH2:11][C:12]1([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C:27]3=[O:32])=[C:22]([CH3:33])[CH:21]=2)=[O:18])[CH2:16][CH2:15][O:14][CH2:13]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:1]([C:3]1[S:7][C:6]([C:8]([NH:11][C:12]2([C:17](=[O:18])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C:27]4=[O:32])=[C:22]([CH3:33])[CH:21]=3)[CH2:16][CH2:15][O:14][CH2:13]2)=[O:10])=[CH:5][CH:4]=1)#[CH:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 450847505-Ethynylthiophene-2-carboxylic acidHCID 688706453-amino-N-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]tetrahydro-furan-3-carboxamide

Product 1

HCID 116121845-Ethynyl-N-{3-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]-tetrahydrofuran-3-yl}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1a from 5-ethynylthiophene-2-carboxylic acid and 3-amino-N-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]tetrahydro-furan-3-carboxamide with TBTU and NMM in DMF.

Sources & evidence

ORD record
ord-bd3264f7afb647378ac809850c56eef8
Source dataset
uspto-grants-2009_07
Patent number
US07563786B2

Reaction notes

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