1-(3',4'-Dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid 2-acetylmethylamino-1-(acetylmethylaminomethyl)ethyl ester → Acetic acid 1-[(acetylmethylamino)methyl]-2-{[1-(3',4'-dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarbonyl]-methylamino}ethyl ester

HRID 76242Notes

Reaction equation

HRID 76242 reaction equation
C(CNCC(O[C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)=[C:22]([F:34])[CH:21]=2)[CH2:19][CH2:18]1)=[O:16])CNCC(=O)C)(=O)C.C([CH2:38][NH:39][CH2:40][CH:41]([O:65][C:66](=[O:68])[CH3:67])[CH2:42][NH:43][CH2:44][C:45]([C:47]1(C2C=CC(C3C=CC(Cl)=C(Cl)C=3)=C(F)C=2)CC1)=[O:46])(=O)C>CN(C1C=CN=CC=1)C>[C:45]([CH2:44][NH:43][CH2:42][CH:41]([O:65][C:66](=[O:68])[CH3:67])[CH2:40][N:39]([C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)=[C:22]([F:34])[CH:21]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:38])(=[O:46])[CH3:47]

Participants

4

Reactant 2

HCID 866988931-(3',4'-Dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid 2-acetylmethylamino-1-(acetylmethylaminomethyl)ethyl ester2×HCID 86698894Acetic acid 1-[(acetylmethylamino)methyl]-2-{[1-(3',4'-dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarbonyl]methylamino}ethyl ester

Product 1

HCID 86698892Acetic acid 1-[(acetylmethylamino)methyl]-2-{[1-(3',4'-dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarbonyl]-methylamino}ethyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Note that although the procedure is similar to that utilized to synthesize C4 (second method, see Example 5), with the exception that also DMAP was added in the coupling step of Example 5 but not of Example 6, the isolated product is different, being acetic acid 1-[(acetylmethylamino)methyl]-2-{[1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarbonyl]methylamino}ethyl ester in Example 6 and 1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid 2-acetylmethylamino-1-(acetylmethylaminomethyl)ethyl ester in Example 5.

Sources & evidence

ORD record
ord-2ade16eee5484b7081ed8e646a8ab0a8
Source dataset
uspto-grants-2014_09
Patent number
US08835494B2

Reaction notes

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