HCID 57848796, compound → HCID 178486243, compound

HRID 736276Notes

Reaction equation

HRID 736276 reaction equation
[CH3:1][N:2]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:3][C:4]([C:6]1[S:36][C:9]2[N:10](C(OC(C)(C)C)=O)[N:11]=[C:12]([NH:13][C:14](=[O:28])[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][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(CN5CCOCC5)C=4)C=3C=2)=O)=CC=1>CO>[CH3:1][N:2]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:3][C:4]([C:6]1[S:36][C:9]2[NH:10][N:11]=[C:12]([NH:13][C:14](=[O:28])[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:16]=3)[C:8]=2[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 57848796HCID 57848796, compoundHCID 57848816HCID 57848816, compound

Product 1

HCID 178486243HCID 178486243, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 257 mg (0.44 mmol) of an approximately 70:30 mixture of tert-butyl 5-(N′-methyl-N′-phenylhydrazinocarbonyl)-3-(3-morpholin-4-ylmethylbenzoylamino)thieno[2,3-c]pyrazole-1-carboxylate and tert-butyl 5-(N′-(4-chlorophenyl)-N′-methylhydrazinocarbonyl)-3-(3-morpholin-4-ylmethylbenzoylamino)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). 105 mg of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-3-morpholin-4-ylmethylbenzamide are thus obtained in the form of a yellow powder melting from 168 to 178° C. 1H NMR (400 MHz, (CD3)2SO-d6, δ in ppm): observation of the salt of the expected structure, with an 80%-20% mixture of conformers, such that: 3.16 (partially masked broad m, 2H); 3.18 (s, 3H); 3.32 (broad m, 2H); 3.63 (broad m, 2H); 3.98 (m, 2H); 4.44 (broad s, 2H); 6.77 (t, J=7.5 Hz, 0.8H); 6.82 (d, J=8.0 Hz, 1.6H); 6.94 (t, J=8.0 Hz, 0.2H); 7.02 (d, J=8.0 Hz, 0.4H); 7.22 (t, J=8.0 Hz, 1.6H); 7.31 (d, J=8.0 Hz, 0.4H); 7.66 (t, J=8.0 Hz, 1H); 7.74 (d, J=8.5 Hz, 1H); 8.15 (m, 3H); 9.70 (s, 0.2H); 10.0 (broad multiplet, 1H); 10.75 (s, 0.8H); 11.25 (s, 0.2H); 11.35 (s, 0.8H); 12.95 (very broad m, 1H).

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-4b80c3eddae549698392d59e6ac2fd0e
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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