Triethylamine → HCID 59577878, compound

HRID 2194289Notes

Reaction equation

HRID 2194289 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:11]2=[O:20])=[CH:6][CH:5]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[S:31](Cl)(=[O:33])=[O:32].CCN(CC)CC>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[S:31]([N:17]1[CH2:16][CH2:15][C:12]2([C:11](=[O:20])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)[CH2:19][CH2:18]1)(=[O:32])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chlorideHCID 667427592-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 59577878HCID 59577878, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 37.7 mg (0.12 mmol) 2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one, 29.7 mg (example 251, step A), 0.132 mmol), 2-chloro-6-methylbenzene-1-sulfonyl chloride and 36.4 mg (0.36 mmol) NEt3 in 2 mL DCM was stirred for 16 h at room temperature. The mixture was evaporated to dryness and the residue was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 14.7 mg (24%) of the title compound. MS (ESI): 503.4 (MH+).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was subjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-b6595134caf941a48a9d89b5a48511bc
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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