Triethylamine → HCID 58531563, compound

HRID 1889705Notes

Reaction equation

HRID 1889705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][C:32]1[C:33]([OH:46])=[C:34]([S:42](Cl)(=[O:44])=[O:43])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1>C(Cl)Cl>[Cl:31][C:32]1[C:33]([OH:46])=[C:34]([S:42]([N:15]([CH2:14][C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)(=[O:44])=[O:43])[CH:35]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58531372HCID 58531372, compound2×HCID 58531652HCID 58531652, compound

Product 1

HCID 58531563HCID 58531563, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(4′-Chlorobiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine (Compound A of Example 232, 200 mg, 0.6 mmol, 1.0 eq) was dissolved in dry DCM (20 mL) then stirred and cooled to 0° C. Triethylamine (186 mg, 1.86 mmol, 3.0 eq) was added slowly and the mixture was stirred for 30 minutes. 3-Chloro-2-hydroxy-5-(trifluoromethyl)benzene-1-sulfonyl chloride (180 mg 0.6 mmol 1.0 eq) dissolved in DCM was added to the above solution and the resulting mixture was stirred for 12 h at ambient temperature. The solution was concentrated under reduced pressure and the residue was purified by silica gel (240-280) column chromatography using 20-30% ethyl acetate/hexane as the eluent to afford the title compound (0.2 g, 56%). 1H NMR (400 MHz, CD3OD) δ 7.92 (d, 1H), 7.79 (d, 1H), 7.43 (d, 5H), 7.32-7.29 (t, 1H), 7.27-7.25 (m, 2H), 7.23 (s, 1H), 7.15-7.13 (d, 1H), 6.98-6.94 (t, 2H), 4.89 (s, 1H), 4.58-4.53 (d, 2H). MS (ESI): 585.8 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. additionwas added to the above solution
  3. stirringthe resulting mixture was stirred for 12 h at ambient temperature
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel (240-280) column chromatography

Sources & evidence

ORD record
ord-6d41bddec695489a82e6dbf9e1889004
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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