Acetic Acid → N-(5-((1S,3S)-3-(5-acetamido-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(3-methoxyphenyl)acetamide
Reaction equation
[C@H:1]1([C:13]2[S:17][C:16]([NH2:18])=[N:15][N:14]=2)[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH2:2]1.[C:19](O)(=[O:21])[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:56][O:57][C:58]1[CH:59]=[C:60]([CH2:64][C:65]([OH:67])=O)[CH:61]=[CH:62][CH:63]=1>CN(C)C=O.O>[C:19]([NH:12][C:10]1[S:11][C:7]([C@H:3]2[CH2:4][CH2:5][CH2:6][C@H:1]([C:13]3[S:17][C:16]([NH:18][C:65](=[O:67])[CH2:64][C:60]4[CH:61]=[CH:62][CH:63]=[C:58]([O:57][CH3:56])[CH:59]=4)=[N:15][N:14]=3)[CH2:2]2)=[N:8][N:9]=1)(=[O:21])[CH3:20]Participants
8
Reactant 5
HCID 176Acetic Acid
HCID 15719(3-Methoxyphenyl)acetic acid
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 867191195,5'-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazol-2-amine)Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of 5,5′-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazol-2-amine) (50 mg, 0.18 mmol), acetic acid (1 eq), HATU (202 mg, 0.53 mmol), and DIPEA (73 mg, 0.57 mmol) in N,N-dimethylformamide (2 ml) was heated to 50° C. for 2 h, then 3-methoxy-2-phenylacetic acid was added. The mixture was heated at 50° C. overnight and then poured into water (20 ml), the precipitate was filtered to give the crude product. The crude product was purified by a standard method to give the desired product.
Workup
- filtrationthe precipitate was filtered
- customto give the crude product
- customThe crude product was purified by a standard method
Sources & evidence
- ORD record
- ord-fbc2ecf2842b4db7be83c6e217c61c67
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029531B2
Reaction notes
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