Benzylamine → HCID 15489612, compound

HRID 580942Notes

Reaction equation

HRID 580942 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([NH:17][C:18]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:19])[CH:12]=[CH:13][C:14]=1[CH2:15]O.C(N(CC)CC)C.[CH2:43]([NH2:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[CH2:43]([N:50]1[CH2:7][CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([NH:17][C:18]([C:20]3[C:21]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:35])[F:34])=[CH:30][CH:31]=4)=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:19])[CH:10]=2)[CH2:15]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15491254HCID 15491254, compound

Product 1

HCID 15489612HCID 15489612, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methanesulfonyl chloride (0.041 mL) was added to a 0° C. solution of 4'-trifluoromethyl-biphenyl-2-carboxylic acid-[3-(2-hydroxy-ethyl)-4-hydroxymethyl-phenyl]-amide (100 mg, 0.24 mmol) and triethylamine (0.084 mL) in THF (2 mL). TLC showed complete reaction after 30 min. Benzylamine (0.132 mL) was added and the contents stirred for 18 hrs at 25° C. and 60 hrs at 50° C. The solvent was removed under vacuum, the residue dissolved in methylene chloride (15 mL), washed with pH9 buffer, phases separated, and the organic phase dried with magnesium sulfate. Removal of the solvent under vacuum gave the crude product as a white solid (204 mg), which was repulsed in CDCl3 filtered off and dried to give the product as a white solid (46 mg, 39%). mp=230-32° C.

Workup

  1. customreaction after 30 min
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in methylene chloride (15 mL)
  4. washwashed with pH9 buffer
  5. customphases separated
  6. dry with materialthe organic phase dried with magnesium sulfate
  7. customRemoval of the solvent under vacuum
  8. customgave the crude product as a white solid (204 mg), which
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-f0a5398b831c411cbd4cde0b022c3f22
Source dataset
uspto-grants-1999_07
Patent number
US05919795

Reaction notes

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