Cyanoacetic acid → HCID 118939087, compound

HRID 524018Notes

Reaction equation

HRID 524018 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].Cl.[F:8][C:9]1([F:34])[CH2:11][CH:10]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH2:20][N:19]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([NH2:33])[CH3:32])=[CH:27][CH:26]=1)[CH2:18][CH2:17]2.CCN(C(C)C)C(C)C>C(#N)C>[C:1]([CH2:3][C:4]([NH:33][C@H:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:19]2[CH2:18][CH2:17][C:16]3[C:21](=[CH:22][CH:23]=[C:14]([O:13][CH2:12][CH:10]4[CH2:11][C:9]4([F:34])[F:8])[CH:15]=3)[CH2:20]2)=[CH:26][CH:27]=1)[CH3:32])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 118939116HCID 118939116, compound

Product 1

HCID 118939087HCID 118939087, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.70 mg (20.0 μmol) Cyanoacetic acid, 4.09 mg (10.0 μmol) (S)-1-{4-[6-(2,2-difluoro-cyclopropylmethoxy)-3,4-dihydro-1H-isoquinolin-2-ylmethyl]-phenyl}-ethylamine hydrochloride (example XXXIII.1) and 6.88 μL (40.0 μmol) DIPEA in 0.5 mL ACN are stirred at r.t. Then 4.18 mg (15.0 μmol) CIP are added and the resulting mixture is stirred at r.t. over night. The reaction is quenched by the addition of 25 μL aq. K2CO3 solution (c=3 mol/L), filtered over basic aluminum oxide and concentrated by evaporation.

Workup

  1. customare stirred at r.t
  2. additionThen 4.18 mg (15.0 μmol) CIP are added
  3. customThe reaction is quenched by the addition of 25 μL aq. K2CO3 solution (c=3 mol/L)
  4. filtrationfiltered over basic aluminum oxide
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d723e08b62de4815a7d271ee030815f9
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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