Triethylamine → HCID 87834352, compound

HRID 404931Notes

Reaction equation

HRID 404931 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([OH:22])[CH3:21])[S:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:32][S:33]([O:22][CH:20]([C:18]1[S:17][N:16]=[C:15]([C:12]2[S:11][C:10]([O:9][C:8]3[CH:23]=[CH:24][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[CH:6][CH:7]=3)=[N:14][CH:13]=2)[N:19]=1)[CH3:21])(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69435316HCID 69435316, compound

Product 1

HCID 87834352HCID 87834352, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 100D (136 g, 0.0037 mol), triethylamine (0.95 g, 0.0094 mol) and 4-(dimethylamino)pyridine in dichloromethane at 0° C. was added methanesulfonyl chloride (0.52 g, 0.0045 mol) drop wise and the mixture was stirred for 2 hours at room temperature. More dichloromethane was added and the organic layer was washed with water, then brine and dried over magnesium sulfate and filtered. The filtrate was concentrated to give 1.5 g of product as a clear oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=6.25 Hz, 6H) 1.90 (d, J=6.62 Hz, 3H) 3.15 (s, 3H) 4.45-4.61 (m, 1H) 6.10 (q, J=6.86 Hz, 1H) 6.87-6.99 (m, 2H) 7.17-7.25 (m, 2H) 7.96 (s, 1H). MS (ESI) m/z 442.0 (M+H)+.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialbrine and dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-18a533282a1642319abf41b7dae0bce4
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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