1-Hydroxybenzotriazole → N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]-2-chloro-6-methylpyridine-3-carboxamide

HRID 2095176Notes

Reaction equation

HRID 2095176 reaction equation
N=C=N.C1C=CC2N(O)N=NC=2C=1.[Cl:14][C:15]1[N:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.[NH2:25][CH2:26][C:27]1[C:28](=[N:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=2)[C:29]([NH2:32])=[N:30][N:31]=1>C(Cl)Cl.CN(C=O)C>[NH2:32][C:29]1[C:28](=[N:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=2)[C:27]([CH2:26][NH:25][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][C:22]([CH3:24])=[N:23][C:15]=2[Cl:14])=[N:31][N:30]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1217242-Chloro-6-methylnicotinic acidHCID 160435CarbodiimideHCID 178510680HCID 178510680, compound

Product 1

HCID 178425854N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]-2-chloro-6-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 mL reaction vessel containing PS-carbodiimide (2 eq, 175 mg) and HOBt (1.7 eq, 20 mg) was added a solution of 2-chloro-6-methylnicotinic acid (1.5 eq, 0.12 mmol) in anhydrous CH2Cl2 (2 mL) and anhydrous DMF (0.2 mL). The reaction mixture was stirred at ambient temperature under argon for 30 minutes before a solution of 5-aminomethyl-4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (20 mg, 0.079 mmol) in anhydrous DCM (3 mL) and anhydrous DMF (0.7 mL) was added. The reaction mixture was further stirred for approximately 16 hours before it was filtered, washed with DCM (3×3 mL) and concentrated under reduced pressure. The title compound was obtained as a yellow powder (yield 26%). MS (m/z, ES+): 406 (Cl35M+1, 20%), 408 (Cl37M+1, 10%).

Workup

  1. customTo a 10 mL reaction vessel
  2. additionwas added
  3. filtrationwas filtered
  4. washwashed with DCM (3×3 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2870be0331a47f39784ffe0c5e09e10
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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