Aniline → HCID 67358757, compound

HRID 2065687Notes

Reaction equation

HRID 2065687 reaction equation
Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[NH2:16][CH:17]([CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].C(N[C@H](C(O)=O)COCC1C=CC=CC=1)(OC(C)(C)C)=O.NC1C=CC=CC=1.ON1C2C=CC=CC=2N=N1.C(O)(C(F)(F)F)=O>CS(C)=O.C(Cl)CCl>[CH2:29]([O:28][CH2:27][CH:17]([NH:16][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1)[C:18](=[O:19])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

9

Reactant 6

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 242660682,6-Dichloroquinoline-3-carboxylic acidHCID 67357823HCID 67357823, compound

Product 1

HCID 67358757HCID 67358757, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with 2-amino-3-benzyloxy-N-phenyl-propionamide (prepared by reaction of N-Boc-O-benzyl-L-serine with aniline in the presence of N-hydroxy-benzotriazole and EDC, followed by deprotection with TFA) in DMSO to provide the title compound in good yield.

Sources & evidence

ORD record
ord-f1ce511d204f4a0b8402949d6763a1fc
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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