Triethylamine → HCID 50913225, compound

HRID 1949078Notes

Reaction equation

HRID 1949078 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2([O:21][CH3:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31].CCN(CC)CC>C(Cl)Cl>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([C:15]2([O:21][CH3:22])[CH2:20][CH2:19][N:18]([S:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[Cl:23])(=[O:32])=[O:31])[CH2:17][CH2:16]2)=[O:14])=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 119671557HCID 119671557, compound

Product 1

HCID 50913225HCID 50913225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25.5 mg (0.078 mmol) 4-Methoxy-piperidine-4-carboxylic acid (4-tert-butyl-phenyl)-amide, hydrochloride, 21.4 mg (0.1 mmol) 2-chlorobenzenesulfonyl chloride and 39.4 mg (0.39 mmol) NEt3 in 1.5 mL DCM was stirred for 16 h at room temperature. The mixture was concentrated and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 20.2 mg (56%) of the title compound as light yellow oil. MS (m/e): 465.2 [(M+H)+].

Workup

  1. concentrationThe mixture was concentrated
  2. customsubjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 20.2 mg (56%) of the title compound as light yellow oil

Sources & evidence

ORD record
ord-2f7fabe5519b4ab7b6d5ee8c207d4511
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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