Water → HCID 60141901, compound

HRID 1907165Notes

Reaction equation

HRID 1907165 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]#[C:11][C:12]2[C:13]([CH3:24])=[N:14][CH:15]=[N:16][C:17]=2[N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:5][N:4]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].N1C=CC=CC=1.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([NH:9][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:7][C:6]([C:10]#[C:11][C:12]2[C:13]([CH3:24])=[N:14][CH:15]=[N:16][C:17]=2[N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68295643HCID 68295643, compound

Product 1

HCID 60141901HCID 60141901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 mg (0.31 mmol) 2-Methoxy-5-(4-methyl-6-morpholin-4-yl-pyrimidin-5-ylethynyl)-pyridin-3-ylamine (E-9) in 5 mL DCM is added 70 mg (0.61 mmol) methanesulfonyl chloride and 72 μL (0.91 mmol) pyridine and the reaction mixture is stirred over night at RT. Water (2 mL) is added and the reaction mixture is extracted three times with 4 mL ethylacetate. The combined organic phases are dried over MgSO4 and concentrated under reduced pressure. The crude product is purified by RP chromatography (C18, 20-80% ACN in water containing 1% formic acid). Yield: 32 mg (18%). HPLC-MS: M+H=404; tR=0.65 min.

Workup

  1. extractionthe reaction mixture is extracted three times with 4 mL ethylacetate
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by RP chromatography (C18, 20-80% ACN in water containing 1% formic acid)

Sources & evidence

ORD record
ord-b82accd0e1fa48f9ba044bf2eafc1044
Source dataset
uspto-grants-2013_12
Patent number
US08598157B2

Reaction notes

Loading…