Triethylamine → HCID 87902786, compound

HRID 1795967Notes

Reaction equation

HRID 1795967 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][N:13]2[C:18]=1[C:17](=[O:19])[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH:27]([OH:30])[CH2:28][CH3:29])=[N:14]2)=[O:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][N:13]2[C:18]=1[C:17](=[O:19])[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH:27]([O:30][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:28][CH3:29])=[N:14]2)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69591774HCID 69591774, compound

Product 1

HCID 87902786HCID 87902786, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.024 ml, 0.31 mmol) was added to a 0° C. solution of 3-benzyl-2-(1-hydroxy-propyl)-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid methyl ester (0.007, 0.21 mmol) and triethylamine (0.052 mL, 0.37 mmol) in CH2Cl2 (1.0 mL) and the mixture was stirred at 0° C. for 30 min. The reaction mixture was then quenched with saturated NaHCO3 (3.0 mL), extracted with EtOAc (3×3 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (0.043 g, 50%) which was used without further purification: MS (ESI+) 420 (M++H).

Workup

  1. customThe reaction mixture was then quenched with saturated NaHCO3 (3.0 mL)
  2. extractionextracted with EtOAc (3×3 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00509d7f8e934f44a64857331ff14cf9
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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