Hydrochloric Acid → HCID 178510461, compound

HRID 526506Notes

Reaction equation

HRID 526506 reaction equation
[CH2:1]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=[N:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:22]=[N:23][N:24]([C:26](=[CH:32]N(C)C)[C:27](OCC)=[O:28])[CH:25]=1)#[N:20].Cl.CCN(C(C)C)C(C)C>CC(O)C>[CH2:1]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:27]([OH:28])=[C:26]([N:24]3[CH:25]=[C:21]([C:19]#[N:20])[CH:22]=[N:23]3)[CH:32]=[N:17]2)=[N:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 51370238N-benzyl-6-hydrazinylpyridine-3-carboxamideHCID 117601152ethyl 2-(4-cyano-1H-pyrazol-1-yl)-3-(dimethylamino)acrylate

Product 1

HCID 178510461HCID 178510461, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combined N-benzyl-6-hydrazinylnicotinamide (103 mg, 0.427 mmol) and ethyl 2-(4-cyano-1H-pyrazol-1-yl)-3-(dimethylamino)acrylate (100 mg, 0.427 mmol) in 2-propanol (1.4 mL) and treated with 1.85N HCl (841 mg, 0.427 mmol). The resulting clear mixture was stirred for 2.5 h and then Hunig's base (297 μl, 1.708 mmol) was added and the resulting red solution was stirred at ambient temperature for 2.5 h. The reaction mixture was then concentrated in vacuo and purified using HPLC (20-95% ACN in water, TFA-buffered). Product-containing fractions were concentrated in vacuo to give a solid (volume ˜50 mL). The solid was filtered and dried in vacuum to give the title compound (65.4 mg, 39.8% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.53 (d, J=5.81 Hz, 2H) 7.27 (dq, J=8.46, 4.17 Hz, 1H) 7.31-7.44 (m, 4H) 8.29 (s, 1H) 8.33-8.58 (m, 3H) 8.93 (s, 1H) 8.98 (s, 1H) 9.30 (t, J=5.81 Hz, 1H) 12.33-14.49 (br s, 1H). MS m/z [M+H]+ 386.

Workup

  1. stirringthe resulting red solution was stirred at ambient temperature for 2.5 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. custompurified
  4. concentrationProduct-containing fractions were concentrated in vacuo
  5. customto give a solid (volume ˜50 mL)
  6. filtrationThe solid was filtered
  7. customdried in vacuum

Sources & evidence

ORD record
ord-40c946ccdf374925bf62f010d11731a4
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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