Triethylamine → HCID 57546165, compound

HRID 913957Notes

Reaction equation

HRID 913957 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:15][CH2:16][C:17]2([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH2:12][CH2:13][OH:14])[C:8]2[C:4](=[CH:5][N:6]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[N:7]=2)[CH:3]=1.C(N(CC)CC)C.[CH3:52][S:53](Cl)(=[O:55])=[O:54]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:15][CH2:16][C:17]2([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH2:12][CH2:13][O:14][S:53]([CH3:52])(=[O:55])=[O:54])[C:8]2[C:4](=[CH:5][N:6]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:43])[CH3:44])[N:7]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57546233HCID 57546233, compound

Product 1

HCID 57546165HCID 57546165, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-3-hydroxypropoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (56 mg, 0.086 mmol) and TRIETHYLAMINE (0.036 ml, 0.259 mmol) in DCM (1.5 ml) at 0 C was added METHANESULFONYL CHLORIDE (0.013 ml, 0.173 mmol). The ice bath was removed and stirring continued for 1 h. The reaction was cooled to 0 C and quenched by addition of sat'd sodium bicarbonate. The reaction was diluted with ether and the layers separated. The ethereal was washed with brine, dried over magnesium sulfate, filtered and concentrated to give 69 mg title compound (quantitative yield). LC/MS (HPLC method 1): tR=4.42 min, 726.2(MH)+.

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction was cooled to 0 C
  3. customquenched by addition of sat'd sodium bicarbonate
  4. additionThe reaction was diluted with ether
  5. customthe layers separated
  6. washThe ethereal was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b581175d066245a28acec286ec049f4e
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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