HCID 57848858, compound → HCID 178480826, compound

HRID 736264Notes

Reaction equation

HRID 736264 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][C:18]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:17][CH:16]=3)[C:8]=2[CH:7]=1)=[O:5]>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:16]=[CH:17][C:18]([CH2:21][N:22]4[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]4)=[CH:19][CH:20]=3)[C:8]=2[CH:7]=1)=[O:5]

Participants

3

Reactant 1

HCID 57848858HCID 57848858, compound

Product 1

HCID 178480826HCID 178480826, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.14 g (232 μmol) of tert-butyl 5-(N′-methyl-N′-phenylhydrazinocarbonyl)-3-[4-(4-methylpiperazin-1-ylmethyl)benzoylamino]-thieno[2,3-c]pyrazole-1-carboxylate in 8 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 20 minutes, and then for two further periods of 15 minutes. The reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 35° C. The residue is taken up in 15 mL of diisopropyl ether, triturated, filtered on a sinter funnel, washed twice with 5 mL of diisopropyl ether, suction-filtered and then dried in an oven under vacuum (0.01 kPa) at a temperature in the region of 60° C. 78 mg of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-4-(4-methylpiperazin-1-ylmethyl)benzamide are thus obtained in the form of an off-white solid melting at 246° C. LC-MS-DAD-ELSD: 504(+)=(M+H)(+); 502(−)=(M−H)(−).

Workup

  1. customthe reaction mixture is irradiated at a temperature in the region of 100° C. for 20 minutes
  2. customfor two further periods of 15 minutes
  3. concentrationThe reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 35° C
  4. customtriturated
  5. filtrationfiltered on a sinter funnel
  6. washwashed twice with 5 mL of diisopropyl ether
  7. filtrationsuction-filtered
  8. customdried in an oven under vacuum (0.01 kPa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-b7427ceefd1146839b737129e4c48847
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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