HCID 13772778, compound → HCID 53942979, compound

HRID 868060Notes

Reaction equation

HRID 868060 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:22])=[C:10]([C:14]3[N:15]=[C:16]([CH2:19]NC)[S:17][CH:18]=3)[C:11]=2[F:13])[C:6](=[O:23])[C:5]([C:24]([OH:26])=[O:25])=[CH:4]1)[CH3:2].[CH2:27]([NH:29]CC1SC=C(C2C(F)=C3C(C(=O)C(C(O)=O)=CN3CC)=CC=2F)N=1)C.NCC1SC=C(C2C(F)=C3C(C(=O)C(C(O)=O)=CN3CCF)=CC=2F)N=1.FC1C=C2C(=C(F)C=1C1N=C(CNC)SC=1)N(CCF)C=C(C(O)=O)C2=O.C(NCC1SC=C(C2C(F)=C3C(C(=O)C(C(O)=O)=CN3CCF)=CC=2F)N=1)C.NCC1SC=C(C2C(F)=CC3C(=O)C(C(O)=O)=CN4C(C)COC=2C=34)N=1>>[NH2:29][CH2:27][CH2:19][C:16]1[S:17][CH:18]=[C:14]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:23])[C:5]([C:24]([OH:26])=[O:25])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:22])[N:15]=1

Participants

7

Reactant 6

HCID 13772778HCID 13772778, compoundHCID 13772779HCID 13772779, compoundHCID 13772780HCID 13772780, compoundHCID 13772781HCID 13772781, compoundHCID 13772782HCID 13772782, compoundHCID 13772842HCID 13772842, compound

Product 1

HCID 53942979HCID 53942979, compound

Procedure

In similar fashion the following compounds were prepared: 1-Ethyl-6,8-difluoro-1,4-dihydro-7-[2-[(methylamino) methyl]-4-thiazolyl]-4-oxo-3-quinolinecarboxylic acid, mp 172°-174° C. (35a); 7-[2-[(ethylamino)methyl]-4-thiazolyl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 155°-157° C. (35b); 7-[2-(aminomethyl)-4-thiazolyl]-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 216°-218° C. (35c); 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-[2[(methylamino)methyl]-4-thiazolyl]-4-oxo-3quinolinecarboxylic acid, mp 214°-215° C. (35d); 7-[2-[(ethylamino)methyl]-4-thiazolyl]-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 197°-201° C. (35e), and 10-[2-(aminomethyl)-4-thiazolyl]-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, mp 229°-231° C. (35f).

Workup

  1. customIn similar fashion the following compounds were prepared

Sources & evidence

ORD record
ord-4a2296e734b94fbaae0d6b55e7aefcb4
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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