Tris(hydroxymethyl)aminomethane → HCID 22707808, compound

HRID 353325Notes

Reaction equation

HRID 353325 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C:11]1([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10].CN1CCOCC1.[F:44][C:45]1[CH:53]=[CH:52][CH:51]=[CH:50][C:46]=1[C:47](Cl)=[O:48].C(O)C(N)(CO)CO>ClCCl>[OH:7][NH:8][C:9]([C:11]1([S:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][N:14]([C:47]([C:46]2[CH:50]=[CH:51][CH:52]=[CH:53][C:45]=2[F:44])=[O:48])[CH2:13][CH2:12]1)=[O:10]

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 79724-MethylmorpholineHCID 98082-Fluorobenzoyl chlorideHCID 20735474HCID 20735474, compound2×

Product 1

HCID 22707808HCID 22707808, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-tetrahydropyranoxy)-4[[4-(4-trifluoromethylphenoxy)phenyl]sulfonyl]-4-piperidinecarboxamide, the product of Example 94, (50 mg) dissolved in dichloromethane (2.5 mL) was added PS-NMM (135 mg, Argonaut) and 2-fluorobenzoyl chloride (12.1 [L) and stirred for 2 hours. To the reaction mixture was added PS-trisamine (50 mg, Argonaut) and the mixture was stirred 1 hour. The reaction mixture was filtered and washed with dichloromethane (2×2 mL) and methanol (1×2 mL). The combined organics were evaporated to afford N-hydroxy-4[[4-(4-trifluoromethylphenoxy)phenyl]-sulfonyl]-1-(2-fluorophenylcarbonyl)-4-piperidinecarboxamide (53.5 mg) as a white solid. MS (ES) m/z 583 (M+H)+.

Workup

  1. stirringthe mixture was stirred 1 hour
  2. filtrationThe reaction mixture was filtered
  3. washwashed with dichloromethane (2×2 mL) and methanol (1×2 mL)
  4. customThe combined organics were evaporated

Sources & evidence

ORD record
ord-8e19cedd3c22463e83eaeae7735ce9d8
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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