Dimethylformamide → HCID 67309452, compound

HRID 406908Notes

Reaction equation

HRID 406908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:18]([OH:20])=O)[N:11]([N:13]=[CH:14][N:15]([CH3:17])[CH3:16])N=2)=[CH:4][CH:3]=1.[CH:21]1[CH:22]=[CH:23][C:24]2[N:29](O)N=[N:27][C:25]=2C=1.[CH3:31]CN=C=NCCCN(C)C.Cl.CC[N:45]([CH:49]([CH3:51])C)[CH:46]([CH3:48])C.CN([CH:55]=[O:56])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([C:18]([NH:29][C:24]3[CH:25]=[N:27][C:21]([N:45]4[CH2:46][CH2:48][CH:55]([OH:56])[CH2:51][CH2:49]4)=[CH:22][CH:23]=3)=[O:20])[N:11]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[CH:31]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67305383HCID 67305383, compound

Product 1

HCID 67309452HCID 67309452, compoundYield 37%

Procedure

To a mixture of 5-(4-chlorophenyl)-2-(dimethylamino-methyleneamino)-2H-pyrazole-3-carboxylic acid (Example 18A, 0.175 g, 0.59 mmol) and DMF (2 mL) was added HOBT (0.039 g, 0.3 mmol), EDCI HCl (0.33 g, 1.7 mmol) and DIPEA (0.15 g, 1.18 mmol). The resulting mixture was stirred at room temperature for 15 min. Example 18C was then added and the mixture was stirred at room temperature overnight. Reaction mass was quenched into water, solid obtained was filtered and washed with water. Pale brown solid (Example 18D, 0.1 g, 37% yield) obtained was taken to the next step without purification. LC-MS, [M+H]+=467.

Workup

  1. additionExample 18C was then added
  2. stirringthe mixture was stirred at room temperature overnight
  3. customReaction mass
  4. customwas quenched into water, solid
  5. customobtained
  6. filtrationwas filtered
  7. washwashed with water
  8. customPale brown solid (Example 18D, 0.1 g, 37% yield) obtained
  9. customwas taken to the next step without purification

Sources & evidence

ORD record
ord-529014bbeb67473e89dc4a2106b87990
Source dataset
uspto-grants-2014_06
Patent number
US08754211B2

Reaction notes

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