HCID 68697521, compound → HCID 68695159, compound

HRID 1157674Notes

Reaction equation

HRID 1157674 reaction equation
[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH2:15][C:16]([NH:18][NH:19]C(OC(C)(C)C)=O)=[O:17])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH2:15][C:16]([NH:18][NH2:19])=[O:17])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 1

HCID 68697521HCID 68697521, compound

Product 1

HCID 68695159HCID 68695159, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Mix a solution of tert-butyl 2-{[1-(3-chloro-4-cyano-2-methylphenyl)pyrrolidin-2-yl]acetyl}hydrazinecarboxylate (0.897 g, 2.35 mmol) in trifluoroacetic acid at ambient temperature for 30 min. Remove the solvent under reduced pressure, dissolve the residue into methanol and apply to a cationic exchange column (10 g Isolute SCX-2). Elute the column with methanol then 2N methanolic ammonia. Concentrate the methanolic ammonia fractions under reduced pressure to obtain the title compound. (0.577 g, 88%) mass spectrum (m/e): 279.1 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.41 (d, 1H), 6.82 (d, 1H), 7.30 (bs, 1H), 4.28 (t, 1H), 3.82 (m, 1H) 3.73 (s. 2H), 3.00 (m, 1H), 2.54 (m, 1H), 2.56 (s, 3H), 2.40 (s, 3H), 1.80-2.10 (m. 3H).

Workup

  1. customRemove the solvent under reduced pressure
  2. dissolutiondissolve the residue into methanol
  3. washElute the column with methanol
  4. concentrationConcentrate the methanolic ammonia fractions under reduced pressure

Sources & evidence

ORD record
ord-7abe7befd22b4b96aae8eaf56b35647f
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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