HCID 66808275, compound → HCID 67249384, compound

HRID 883838Notes

Reaction equation

HRID 883838 reaction equation
Cl[C:2]1[N:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]1[N:7]2[N:12]=[C:13]([CH3:15])[CH:14]=1.[NH2:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[CH:20]=[CH:19][C:18]=1[S:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1>C(O)C>[CH3:15][C:13]1[CH:14]=[C:6]2[N:5]=[CH:4][C:3]3[C:8](=[N:9][CH:10]=[N:11][C:2]=3[NH:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=4)[CH:20]=[CH:19][C:18]=3[S:35][C:36]3[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=3)[N:7]2[N:12]=1

Participants

4

Reactant 2

HCID 66808275HCID 66808275, compoundHCID 86654886HCID 86654886, compound

Product 1

HCID 67249384HCID 67249384, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 4a (88 mg, 0.40 mmol) was reacted with 4-[2-Amino-4-(3-trifluoromethyl-benzyloxy)-phenylsulfanyl]-phenol (151 mg, 0.40 mmol) in 5 mL of ethanol at 70° C. with stirring for 6 hours. After cooling to room temperature the product was isolated by suction filtration and was triturated with diethyl ether to give the title compound as a pale yellow solid (123 mg, 50%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 10.45 (s, 1H) 9.65 (s, 1H) 9.34 (s, 1H) 8.57 (s, 1H) 7.62-7.85 (m, 4H) 7.09-7.21 (m, 4H) 7.02 (dd, J=3.02 Hz, J=8.74 Hz, 1H) 6.74 (s, 1H) 6.65 (dd, J=2.19 Hz, J=8.74 Hz, 2H) 5.23 (s, 2H) 2.48 (s, 3H); (ESI+) m/z 575 (M+H−Cl)+; (ESI−) m/z 573 (m−H−Cl)−.

Workup

  1. customwas isolated by suction filtration
  2. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-7b1ce3377cfc4eaaa23ed05cb91351f9
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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