Dimethylformamide → HCID 67309452, compound
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]=1Participants
6
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
- additionExample 18C was then added
- stirringthe mixture was stirred at room temperature overnight
- customReaction mass
- customwas quenched into water, solid
- customobtained
- filtrationwas filtered
- washwashed with water
- customPale brown solid (Example 18D, 0.1 g, 37% yield) obtained
- customwas taken to the next step without purification
Sources & evidence
- ORD record
- ord-408fc7abdf874761a9af0ab9da17c047
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580959B2
Reaction notes
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