Pyridine → HCID 86647059, compound

HRID 1621738Notes

Reaction equation

HRID 1621738 reaction equation
[CH3:1][O:2][C:3]1[CH:55]=[CH:54][C:6]([CH2:7][N:8]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:31]([OH:44])[C:32]4[CH:37]=[CH:36][C:35]([S:38]([N:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])=[CH:34][CH:33]=4)[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:62][S:63](Cl)(=[O:65])=[O:64]>C(Cl)Cl.O.CCOC(C)=O.O1CCOCC1>[CH3:62][S:63]([O:44][CH:31]([C:18]1[CH:19]=[N:20][C:21]([NH:22][C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[C:16]([C:11]2[N:10]=[C:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:55][CH:54]=3)[CH2:45][C:46]3[CH:47]=[CH:48][C:49]([O:52][CH3:53])=[CH:50][CH:51]=3)[N:14]=[C:13]([CH3:15])[N:12]=2)[CH:17]=1)[C:32]1[CH:37]=[CH:36][C:35]([S:38](=[O:40])(=[O:39])[N:41]([CH3:43])[CH3:42])=[CH:34][CH:33]=1)(=[O:65])=[O:64]

Participants

8

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 666120144-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide

Product 1

HCID 86647059HCID 86647059, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide (12.9 mg, 0.017 mmol) in DCM (0.2 mL) was treated with pyridine (20 μL, 0.25 mmol) followed by methanesulfonyl chloride (20 μL, 0.258 mmol). The mixture was allowed to stand overnight. Some crystals formed. The crystals were colorless and insoluble in DCM, but soluble in water. The mixture was diluted with DCM (10 mL) and washed with saturated aqueous NaHCO3 (5 mL). The DCM layer was dried and concentrated to give a yellow solid which was soluble in DCM, but insoluble in EtOAc and sparingly soluble in dioxane. The crude product was taken on directly to the next step.

Workup

  1. customSome crystals formed
  2. washwashed with saturated aqueous NaHCO3 (5 mL)
  3. dry with materialThe DCM layer was dried
  4. concentrationconcentrated
  5. customto give a yellow solid which

Sources & evidence

ORD record
ord-ed91ee1cf47b41d0b651a6b45ec87666
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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