Acetonitrile → 5-(3,3-dimethyl-but-1-ynyl)-3-{N-(4-methyl-cyclohexanecarbonyl)-N'-[2-(pyridin-3-yloxy)-ethyl]-hydrazino}-thiophene-2-carboxylic acid

HRID 336053Notes

Reaction equation

HRID 336053 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C:15]([CH:17]2[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]2)=[O:16])[NH2:14])[CH:6]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH:34]=O)[CH:27]=1.C(#N)C.FC(F)(F)C(O)=O>O>[CH3:1][C:2]([CH3:24])([CH3:25])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C:15]([CH:17]2[CH2:18][CH2:19][CH:20]([CH3:23])[CH2:21][CH2:22]2)=[O:16])[NH:14][CH2:34][CH2:33][O:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 45079808(Pyridin-3-yloxy)-acetaldehydeHCID 583558525-(3,3-dimethyl-but-1-ynyl)-3-[N-(4-methyl-cyclohexanecarbonyl)-hydrazino]-thiophene-2-carboxylic acid

Product 1

HCID 583558625-(3,3-dimethyl-but-1-ynyl)-3-{N-(4-methyl-cyclohexanecarbonyl)-N'-[2-(pyridin-3-yloxy)-ethyl]-hydrazino}-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was synthesized from 5-(3,3-dimethyl-but-1-ynyl)-3-[N-(4-methyl-cyclohexanecarbonyl)-hydrazino]-thiophene-2-carboxylic acid and (pyridin-3-yloxy)-acetaldehyde in a manner similar to that of Example 131. MS (m/z): 484.0 [M−H]+; HPLC retention time: 3.44 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Sources & evidence

ORD record
ord-5e295b25d37d4cae8ab0b91abec47795
Source dataset
uspto-grants-2014_11
Patent number
US08884030B2

Reaction notes

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