Benzenamine, 4-(4-morpholinyl)- → HCID 11591967, compound

HRID 729295Notes

Reaction equation

HRID 729295 reaction equation
Cl[C:2]1[C:3](=[O:26])[N:4]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([F:25])[F:24])=[CH:18][CH:17]=2)[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1>CC#N>[F:24][CH:23]([F:25])[O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:4]2[C:3](=[O:26])[C:2]([NH:37][C:36]3[CH:35]=[CH:34][C:33]([N:30]4[CH2:31][CH2:32][O:27][CH2:28][CH2:29]4)=[CH:39][CH:38]=3)=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:5]2(=[O:14])=[O:13])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 686617234-Chloro-2-[4-(difluoromethoxy)benzyl]-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11591967HCID 11591967, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-[4-(difluoromethoxy)benzyl]-5-phenylisothiazol-3(2H)-one 1,1-dioxide (40 mg, 0.1 mmol) and 4-morpholinoaniline (36 mg 0.2 mmol) were mixed in MeCN (1 ml). The reaction mixture was heated in a microwave reactor at 150° C. for 15 mins and then evaporated to dryness. The residue was purified by column chromatography (ISOLUTE SI, 5 g/25 ml), eluting with DCM, then MeOH/DCM (1:99) and a product mixture was obtained. It was further purified by re-chromatography (ISOLUTE SI, 5 g/25 ml), eluting with EtOAc/heptane (10:90, then 25:75), to give the title compound (14 mg, 26%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.96-2.99 (m, 4H), 3.78-3.81 (m, 4H), 4.86 (s, 2H), 6.47-6.51 (m, 2H), 6.50 (t, J=74 Hz, 1H), 6.57-6.60 (m, 2H), 7.09-7.13 (m, 7H), 7.17-7.22 (m, 1H), 7.52-7.57 (m, 2H); 13C NMR (100 MHz, CDCl3): δ 42.8, 49.4, 66.6, 109.7, 115.3, 115.8 (t, J=259 Hz), 119.6, 123.5, 124.7, 127.9, 128.9, 129.3, 130.6, 131.2, 131.5, 149.1, 151.2, 159.3; Mass Spectrum: M−H+ 540.

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by column chromatography (ISOLUTE SI, 5 g/25 ml)
  3. washeluting with DCM
  4. customMeOH/DCM (1:99) and a product mixture was obtained
  5. customIt was further purified by re-chromatography (ISOLUTE SI, 5 g/25 ml)
  6. washeluting with EtOAc/heptane (10:90

Sources & evidence

ORD record
ord-6a9477275a0a4b8dadb5ac87b5e705bd
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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