Water → HCID 60142043, compound

HRID 1907169Notes

Reaction equation

HRID 1907169 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][N:26]1[C:30]([S:31](Cl)(=[O:33])=[O:32])=[CH:29][CH:28]=[N:27]1.N1C=CC=CC=1.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([NH:9][S:31]([C:30]2[N:26]([CH3:25])[N:27]=[CH:28][CH:29]=2)(=[O:33])=[O:32])=[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 224726211-Methyl-1H-pyrazole-5-sulfonyl chlorideHCID 68295643HCID 68295643, compound

Product 1

HCID 60142043HCID 60142043, 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 111 mg (0.61 mmol) 1-methyl-1H-pyrazole-5-sulfonyl chloride and 72 μL (0.97 mmol) pyridine and the reaction mixture is stirred over night at RT. Water (2 mL) is added, the mixture is shaken for five minutes, the aqueous phase is separated and is extracted three times with 4 mL DCM. 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 (22%). HPLC-MS: M+H=470; tR=0.78 min.

Workup

  1. stirringthe mixture is shaken for five minutes
  2. customthe aqueous phase is separated
  3. extractionis extracted three times with 4 mL DCM
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by RP chromatography (C18, 20-80% ACN in water containing 1% formic acid)

Sources & evidence

ORD record
ord-81ad411a02b04056bd2071e5f27c2637
Source dataset
uspto-grants-2013_12
Patent number
US08598157B2

Reaction notes

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