Dichloromethane → HCID 66611809, compound

HRID 1812332Notes

Reaction equation

HRID 1812332 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:32](O)[C:33]([F:36])([F:35])[F:34])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.[Cl:49]CCl.C(N(CC)CC)C.CS(Cl)(=O)=O>>[Cl:49][CH:32]([C:18]1[CH:17]=[C:16]([C:11]2[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:48][CH:47]=3)[CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[N:10]=2)[C:21]([NH:22][C:23]2[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=2)=[N:20][CH:19]=1)[C:33]([F:35])([F:34])[F:36]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66611181HCID 66611181, compound

Product 1

HCID 66611809HCID 66611809, compound

Procedure

To a solution of (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanol (1.03 g, 1.547 mmol) in dichloromethane (20 mL, 1.547 mmol) was added triethylamine (0.539 mL, 3.87 mmol) and methanesulfonyl chloride (0.244 mL, 3.09 mmol) at 0° C. and the mixture was stirred at the same temperature for 3 h, and warmed up to room temperature and stirred for another 2 h. The reaction was quenched with saturated aqueous NH4Cl solution and water at room temperature, and the separated aqueous layer was extracted with DCM (2×50 mL) and the combined organic layers were dried over Na2SO4 and concentrated and dried under vacuum to give the crude product. m/z (ESI, +ve ion) 684 (M+H)+. The material was used directly without further purification.

Workup

  1. stirringstirred for another 2 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution and water at room temperature
  3. extractionthe separated aqueous layer was extracted with DCM (2×50 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-510fae27bf7143cab961912f8a3ec86e
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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