ethyl (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate → ethyl (S)-2-(2-benzoylphenylamino)-3-{3'-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionate

HRID 271845Notes

Reaction equation

HRID 271845 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:46])[C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]C)=[O:37])[CH:30]=2)=[CH:25][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=C[C:56]=1[NH:61][C@@H:62](CC1C=CC(C2C=CC=C(NC)C=2)=CC=1)C(OCC)=O)(=O)C1C=CC=CC=1.C(N(CC)C1C=CC(N=C=O)=CC=1)C>>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:46])[C:36]([NH:38][C:39]3[CH:40]=[CH:41][C:42]([N:61]([CH3:62])[CH3:56])=[CH:43][CH:44]=3)=[O:37])[CH:30]=2)=[CH:27][CH:28]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10371672ethyl (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionateHCID 22348350N,N-Diethyl-4-isocyanatoanilineHCID 69685584ethyl (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionate

Product 1

HCID 10054914ethyl (S)-2-(2-benzoylphenylamino)-3-{3'-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionateYield 75%

Procedure

In a manner similar to the preparation of the ethyl (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate (Example 1h), using 1.0 g (2.1 mmol) of ethyl (S)-2-(2-benzoylphenylamino)-3-(3′-methylaminobiphenyl-4-yl)propionate (Example 1g) and 0.40 g (2.47 mmol) of 4-(diethylamino)phenyl isocyanate, 0.86 g of ethyl (S)-2-(2-benzoylphenylamino)-3-{3′-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionate is isolated with a 75% yield. Melting point: 75° C.

Sources & evidence

ORD record
ord-1b39f3150a264c7182a6af1a8803db33
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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