Butyric Acid → 5'-Butyrylamino-2'-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide

HRID 1678475Notes

Reaction equation

HRID 1678475 reaction equation
[O:1]=[S:2]1(=[O:32])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:25]=4[CH3:31])=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:33](O)(=[O:37])[CH2:34][CH2:35][CH3:36].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[O:32]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([NH:30][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH:27]=[CH:26][C:25]=4[CH3:31])=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 264Butyric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 598223845'-Amino-2'-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1 lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide

Product 1

HCID 1317291315'-Butyrylamino-2'-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-amino-2′-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide (54 mg), butyric acid (11 mg), EDAC (24 mg), HOBT (16 mg) and N-methylmorpholine (24 mg) in dry DMF (1 ml) was stirred at 20 C for 18 h. The mixture was then diluted with water (6 ml) and the resulting colourless solid collected by filtration and dried (42 mg).

Workup

  1. filtrationthe resulting colourless solid collected by filtration
  2. customdried (42 mg)

Sources & evidence

ORD record
ord-0c2d477330bf466fa5cc1f6f171b46ef
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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