Acetohydrazide → HCID 68699551, compound

HRID 1157671Notes

Reaction equation

HRID 1157671 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12](O)=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C(N(CC)C(C)C)(C)C.CN([C:31]([O:35]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:50]([NH:53][NH2:54])(=[O:52])[CH3:51]>CN(C=O)C>[C:50]([NH:53][NH:54][C:31](=[O:35])[CH2:12][CH:11]1[CH2:15][CH2:16][CH2:17][N:10]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=1[CH3:18])(=[O:52])[CH3:51]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68699150HCID 68699150, compound

Product 1

HCID 68699551HCID 68699551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-(3-chloro-4-cyano-2-methylphenyl)proline (0.600 g, 2.268 mmol), N,N-diisopropylethylamine (0.876 g, 6.816 mmol) and TBTU (1.092 g, 3.402 mmol) in DMF add a solution of acetic hydrazide (0.252 g, 3.402 mmols) in DMF. Leave to stand for 30 mins then partition between ethyl acetate and 2N aqueous hydrochloric acid. Extract the organic with 10% (w/w) aqueous sodium carbonate solution, then brine. Dry over magnesium sulphate, filter and concentrate under reduced pressure gives the title compound. (0.598 g, 82%) mass spectrum (m/e): 321 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.77 (s, 1H) 7.60 (bs, 1H) 7.40 (d, 1H), 6.88 (d, 1H), 4.35 (t, 1H), 3.86 (m, 1H), 3.04 (m, 1H), 2.51 (m, 1H), 2.44 (s, 3H), 2.00 (s, 3H), 2.22-1.85 (m. 3H).

Workup

  1. customLeave
  2. customthen partition between ethyl acetate and 2N aqueous hydrochloric acid
  3. extractionExtract the organic with 10% (w/w) aqueous sodium carbonate solution
  4. dry with materialDry over magnesium sulphate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-3214e7a5e8c84500a5896e1e3fa95eba
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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