HCID 57848856, compound → HCID 178480820, compound

HRID 736270Notes

Reaction equation

HRID 736270 reaction equation
[CH3:1][N:2]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:3][C:4]([C:6]1[S:37][C:9]2[N:10](C(OC(C)(C)C)=O)[N:11]=[C:12]([NH:13][C:14](=[O:29])[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[CH:16]=3)[C:8]=2[CH:7]=1)=[O:5].ClC1C=CC(N(C)NC(C2SC3N(C(OC(C)(C)C)=O)N=C(NC(=O)C4C=CC=C(CN5CCN(C)CC5)C=4)C=3C=2)=O)=CC=1>CO>[CH3:1][N:2]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:3][C:4]([C:6]1[S:37][C:9]2[NH:10][N:11]=[C:12]([NH:13][C:14](=[O:29])[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[CH:16]=3)[C:8]=2[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 57848856HCID 57848856, compoundHCID 57848857HCID 57848857, compound

Product 1

HCID 178480820HCID 178480820, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.07 g (116 μmol) of an approximately 70:30 mixture of tert-butyl 5-(N′-methyl-N′-phenylhydrazinocarbonyl)-3-[3-(4-methylpiperazin-1-ylmethyl)-benzoylamino]thieno[2,3-c]pyrazole-1-carboxylate and tert-butyl 5-(N′-(4-chlorophenyl)-N′-methylhydrazinocarbonyl)-3-[3-(4-methylpiperazin-1-ylmethyl)-benzoylamino]thieno[2,3-c]pyrazole-1-carboxylate in 4 mL of methanol is introduced into a microwave oven tube. The tube is stoppered and the reaction mixture is irradiated at a temperature in the region of 100° C. for 30 minutes. The reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is purified by preparative LC/MS (conditions B). 70 mg of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-3-(4-methylpiperazin-1-ylmethyl)benzamide are thus obtained in the form of a yellow powder melting from 149 to 156° C. LC-MS-DAD-ELSD: 502(−)=(M−H)(−); 504(+)=(M+H)(+).

Workup

  1. additionis introduced into a microwave oven tube
  2. customthe reaction mixture is irradiated at a temperature in the region of 100° C. for 30 minutes
  3. concentrationThe reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  4. customThe residue is purified by preparative LC/MS (conditions B)

Sources & evidence

ORD record
ord-76980f3b882c4bf8b6b0d7c22ceee4ef
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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