Methanesulfonyl chloride → HCID 178505145, compound

HRID 1819437Notes

Reaction equation

HRID 1819437 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].CCN(C(C)C)C(C)C>C(Cl)Cl>[N+:16]([C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:7][CH2:6]2)=[N:11][C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:30])([F:31])[F:29])=[N:13][CH:14]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178511544HCID 178511544, compound

Product 1

HCID 178505145HCID 178505145, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (50 mg, 0.11 mmol) were added methanesulfonyl chloride (18 μL, 0.23 mmol) and DIPEA (59 μL, 0.34 mmol) in CH2Cl2 (2 mL). The reaction mixture was stirred at room temperature for 15 min and diluted with CH2Cl2. The organic phase was then washed with 1M Na2CO3 and water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 28 mg (47%) of the title compound, m/z 517.7 [M−1]+

Workup

  1. washThe organic phase was then washed with 1M Na2CO3 and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-fc39700b3d6a4605a7d72ccb6f65c393
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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