Hydrazinecarboxaldehyde → HCID 136338033, compound

HRID 926131Notes

Reaction equation

HRID 926131 reaction equation
[C:1]([C:3]1[C:4]([NH:18][C:19](=[O:23])OCC)=[N:5][CH:6]=[C:7]([CH2:9][N:10]2[CH2:15][C@@H:14]([CH3:16])[O:13][C@@H:12]([CH3:17])[CH2:11]2)[CH:8]=1)#[N:2].[CH:24]([NH:26]N)=O.C([N:30](C(C)C)C(C)C)C>CC(N(C)C)=O>[CH3:17][C@H:12]1[CH2:11][N:10]([CH2:9][C:7]2[CH:6]=[N:5][C:4]3[NH:18][C:19](=[O:23])[N:2]4[N:30]=[CH:24][N:26]=[C:1]4[C:3]=3[CH:8]=2)[CH2:15][C@@H:14]([CH3:16])[O:13]1

Participants

5

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 81531DiisopropylethylamineHCID 86705398HCID 86705398, compound

Product 1

HCID 136338033HCID 136338033, compoundYield 167.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Ethyl 3-cyano-5-(((2S,6R)-2,6-dimethylmorpholino)methyl)pyridin-2-ylcarbamate (35 mg, 0.11 mmol), formyl hydrazine (8 mg, 0.13 mmol) and N-ethyl N-isopropylpropan-2-amine (0.01 mL, 0.055 mmol) were heated in DMA (1 mL) at 125° C. for 15 h. The reaction was cooled to room temperature and purified directly (HPLC, 10-70% ACN-water) to afford the title compound as a solid (29 mg, 84%). 1H NMR (400 MHz, DMSO-d6) δ 1.04 (d, J=6.15 Hz, 6H), 1.73 (t, J=10.67 Hz, 2H), 2.72 (d, J=10.79 Hz, 2H), 3.53-3.66 (m, 4H), 8.45 (s, 1H), 8.57 (s, 1H), 8.62 (s, 1H), 12.82 (br s, 1H).

Workup

  1. custompurified directly (HPLC, 10-70% ACN-water)

Sources & evidence

ORD record
ord-099b4941a87446ddb6b14b7f87af0d4f
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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