Triethylamine → HCID 18473236, compound

HRID 2227392Notes

Reaction equation

HRID 2227392 reaction equation
Cl.[N:2]1([S:8]([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([NH:44][S:45]([C:47]([CH3:50])([CH3:49])[CH3:48])=[O:46])([C:38]2[N:42]([CH3:43])[CH:41]=[N:40][CH:39]=2)[CH2:34][CH2:35][CH:36]=O)=[CH:29][C:28]=1[F:51])#[N:26].[BH3-]C#N.[Na+]>CO.CC(O)=O>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([NH:44][S:45]([C:47]([CH3:50])([CH3:49])[CH3:48])=[O:46])([C:38]2[N:42]([CH3:43])[CH:41]=[N:40][CH:39]=2)[CH2:34][CH2:35][CH2:36][N:5]2[CH2:4][CH2:3][N:2]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)(=[O:10])=[O:9])[CH2:7][CH2:6]2)=[CH:29][C:28]=1[F:51])#[N:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 18473242HCID 18473242, compoundHCID 18473245HCID 18473245, compound

Product 1

HCID 18473236HCID 18473236, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

3-(Piperazin-1-ylsulfonyl) phenol hydrochloride (0.065 g, 0.231 mmol) was dissolved in MeOH (5 mL), neutralized with Et3N (0.032 mL, 0.231 mmol), then treated with N-[1-(4-cyano-3-fluorophenyl)-4-oxo-1-(1-methyl-1H-imidazol-5-yl)butyl]-2-methylpropane-2-sulfinamide (0.086 g, 0.220 mmol). The pH of the solution was adjusted to 5 with HOAc, then NaCNBH3 (0.021 g, 0.330 nunol) was added, and the pH was adjusted again to 5. After stirring at ambient temperature for 18 h, the reaction mixture was concentrated in vacuo, partitioned between CH2Cl2 and aqueous saturated NaHCO3 solution, the aqueous layer washed with CH2Cl2 (2×), the organic layers combined and dried (MgSO4), filtered and concentrated to give the title product. MS(M+1) 617.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 and aqueous saturated NaHCO3 solution
  3. washthe aqueous layer washed with CH2Cl2 (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e02af881543c4e63b1c4d08aa19aa634
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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