Triethylamine → HCID 86647071, compound

HRID 1621889Notes

Reaction equation

HRID 1621889 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:49]=[CH:48][C:11]([CH2:12][N:13]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:14]2[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([C:21]3[CH:22]=[C:23]([CH:36]([OH:38])[CH3:37])[CH:24]=[N:25][C:26]=3[NH:27][C:28]3[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[N:15]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:38][CH:36]([C:23]1[CH:24]=[N:25][C:26]([NH:27][C:28]2[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[C:21]([C:16]2[N:15]=[C:14]([N:13]([CH2:12][C:11]3[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:49][CH:48]=3)[CH2:39][C:40]3[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[N:19]=[C:18]([CH3:20])[N:17]=2)[CH:22]=1)[CH3:37])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 666113881-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol

Product 1

HCID 86647071HCID 86647071, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.164 mL, 2.119 mmol) was added to a solution of 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (331.1 mg, 0.558 mmol) and triethylamine (0.350 mL, 2.510 mmol) in CH2Cl2 (7.5 mL) at 0° C., and the resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was then partitioned between CH2Cl2 (40 mL) and water (30 mL). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethyl methanesulfonate (356.1 mg, 0.530 mmol, 95% yield) as a yellow-brown solid, which was used directly in Step 3.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 (40 mL) and water (30 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (30 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71bba574ace34b8093722aaf940fe5fc
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…