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Water → HCID 66612048, compound

HRID 1812280
Notes
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Reaction equation

HRID 1812280 reaction equation
[CH2:1]([S:3]([C:5]1[CH:6]=[C:7]([C:21]2[N:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[N:22]=2)[C:8]([NH:11][C:12]2[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([F:18])[CH:17]=2)=[N:9][CH:10]=1)=[O:4])[CH3:2].O.S(O)([O-])(=O)=[O:49].S(O)(OO)(=O)=O.[K+]>CO.O1CCOCC1>[CH2:1]([S:3]([C:5]1[CH:6]=[C:7]([C:21]2[N:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)[N:22]=2)[C:8]([NH:11][C:12]2[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([F:18])[CH:17]=2)=[N:9][CH:10]=1)(=[O:49])=[O:4])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 66611542HCID 66611542, compoundHCID 131730192HCID 131730192, compound

Product 1

HCID 66612048HCID 66612048, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a slurry of 4-(5-(ethylsulfinyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.090 g, 0.140 mmol) in 2 mL MeOH, 2 mL dioxane, and 1 mL water was added potassium peroxymonosulfate sulfate (0.172 g, 0.280 mmol). The bright yellow slurry was stirred rapidly overnight. The reaction was partitioned between satd NaHCO3 and DCM. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography (25 g column) using 20 to 100% EtOAc/hexane. The product-containing fractions were concentrated to afford 4-(5-(ethylsulfonyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.066 g, 0.100 mmol, 71.6% yield) as a yellow solid. m/z (ESI, +ve ion) 660 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 11.91 (s, 1H), 8.80 (d, J=2.7 Hz, 1H), 8.43 (d, J=2.7 Hz, 1H), 8.15-8.33 (m, 2H), 7.14-7.25 (m, 4H), 6.80-6.93 (m, 4H), 4.87 (s, 2H), 4.83 (s, 2H), 4.02 (s, 3H), 3.82 (s, 3H), 3.79 (s, 3H), 3.07-3.22 (m, 1H), 2.82-2.94 (m, 1H), 2.62 (s, 3H), 1.28 (t, J=7.4 Hz, 3H).

Workup

  1. customThe reaction was partitioned between satd NaHCO3 and DCM
  2. extractionThe aqueous layer was extracted with DCM 3 times
  3. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionThe material was treated with DCM
  7. custompurified by silica gel chromatography (25 g column)
  8. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-1c815aa1d59a4a38ad2ee5de32ca8e26
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362241B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes