Triethylamine → HCID 66891823, compound

HRID 216309Notes

Reaction equation

HRID 216309 reaction equation
[CH2:1]([C@H:8]([NH:17][C:18](=[O:37])[C@@H:19]([N:24]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[C:25]1=[O:36])[C@@H:20]([CH3:23])[CH2:21][CH3:22])[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]([C:40]1[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1)#[N:39].C(N(CC)CC)C>ClCCl>[CH2:1]([C@H:8]([NH:17][C:18](=[O:37])[C@@H:19]([N:24]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[C:25]1=[O:36])[C@@H:20]([CH3:23])[CH2:21][CH3:22])[C@H:9]([OH:16])[CH2:10][N:11]([S:46]([C:43]1[CH:42]=[CH:41][C:40]([C:38]#[N:39])=[CH:45][CH:44]=1)(=[O:48])=[O:47])[CH2:12][CH:13]([CH3:14])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 66891641HCID 66891641, compound

Product 1

HCID 66891823HCID 66891823, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 785A (50 mg, 0.098 mmol) was dissolved in dichloromethane (1 mL) and combined with p-cyanobenzenesulfonyl chloride (24 mg, 1.2 equivalents) and triethylamine (41 μL, 3 equivalents) at 25° C. for 16 h. The mixture was quenched with 1N NaHCO3 and extracted with ethyl acetate. The organic layer was evaporated, and the residue was purified using ethyl acetate to give 49 mg (74%) of the title compound.

Workup

  1. customThe mixture was quenched with 1N NaHCO3
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was evaporated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-8d04c7aaae73442db360ec5869053550
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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