Carbodiimide → HCID 178509158, compound

HRID 2095174Notes

Reaction equation

HRID 2095174 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[CH2:10][C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N=C=N.[NH2:18][CH2:19][C:20]1[C:21](=[N:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[C:22]([NH2:25])=[N:23][N:24]=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:14])[CH2:10][C:11]([NH:18][CH2:19][C:20]1[C:21](=[N:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[C:22]([NH2:25])=[N:23][N:24]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 1816593-(Benzyloxy)-3-oxopropanoic acidHCID 178510679HCID 178510679, compound

Product 1

HCID 178509158HCID 178509158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of malonic acid monobenzyl ester (1.5 eq, 0.26 mmol) in anhydrous DMF (3 mL) was added to a 10 mL reaction vessel containing PS-carbodiimide (2 eq, 380 mg). The reaction mixture was stirred at ambient temperature under argon for 10 minutes before a solution of 5-aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (40 mg, 0.17 mmol) in anhydrous DMF (3 mL) was added. The mixture was further stirred for approximately 16 hours before it was filtered, washed with DMF (3×3 mL) and concentrated under reduced pressure. The title compound was obtained in a yield of 38 mg (55%) as a yellow powder with no further purification. MS (m/z, ES+): 411 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 11.40 (brs, 1H, N—H pyrazole), 8.45 (s, 1H, N—H amide), 7.40-7.60 (m, 3H, Ar—H), 7.28-7.35 (m, 5H, Ar—H), 7.05-7.15 (t, 1H, F—Ar—H), 5.15 (s, 2H, benzyl CH2), 4.47 (s, 1H, CHaHb amide), 4.43 (s, 1H, CHaHb amide), 3.35 (2H, CH2 pyrazole-overlap with H2O).

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. washwashed with DMF (3×3 mL)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9cff3f8467084a6a8e00d4caa3fe0a1d
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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