Triethylamine → HCID 49785522, compound

HRID 1621729Notes

Reaction equation

HRID 1621729 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([CH2:6][C:7]2[CH:8]=[C:9]([C:22]3[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([NH2:29])[N:23]=3)[C:10]([NH:13][C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[N:11][CH:12]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[NH2:29][C:24]1[N:25]=[C:26]([CH3:28])[N:27]=[C:22]([C:9]2[CH:8]=[C:7]([CH2:6][N:4]3[CH2:5][CH:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:3]3)[CH:12]=[N:11][C:10]=2[NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59548405HCID 59548405, compound

Product 1

HCID 49785522HCID 49785522, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(5-((3-aminoazetidin-1-yl)methyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (106 mg, 0.269 mmol) and triethylamine (56.2 μL, 0.404 mmol) in DCM (2.7 mL) was treated with MsCl (20.85 μL, 0.269 mmol) and stirred at ambient temperature for 3 h. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated. The crude product was purified via flash chromatography (silica gel) with 100% DCM to 6% 2 M ammonia in MeOH/DCM to give N-(1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)azetidin-3-yl)methanesulfonamide (10 mg, 7% yield) as yellow solid. m/z (ESI, +ve ion) 472.1 (M+H)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washwashed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified via flash chromatography (silica gel) with 100% DCM to 6% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-b2709adc401044f09699e43df873c284
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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