4-Methylmorpholine → (R)-5-Ethynyl-N-{2-methoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}thiophene-2-carboxamide

HRID 229347Notes

Reaction equation

HRID 229347 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@H:12]([CH2:30][O:31][CH3:32])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][C:23]2=[O:28])=[C:18]([CH3:29])[CH:17]=1)=[O:14].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@@H:12]([C:13](=[O:14])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C:23]3=[O:28])=[C:18]([CH3:29])[CH:17]=2)[CH2:30][O:31][CH3:32])=[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 688724282-(R)-amino-3-methoxy-N-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]propionamide

Product 1

HCID 11611953(R)-5-Ethynyl-N-{2-methoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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

Sources & evidence

ORD record
ord-c8915e73a530494a9e024e16ccc687bf
Source dataset
uspto-grants-2009_07
Patent number
US07563786B2

Reaction notes

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