Chloroacetyl chloride → HCID 66610585, compound

HRID 1812010Notes

Reaction equation

HRID 1812010 reaction equation
[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]([CH2:7][N:8]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:31][NH:32][CH2:33][CH2:34][OH:35])[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.[Cl:47][CH2:48][C:49](Cl)=[O:50].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.CO>[CH3:44][O:43][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:46][CH:45]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:31][N:32]([CH2:33][CH2:34][OH:35])[C:49](=[O:50])[CH2:48][Cl:47])[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:42][CH:41]=1

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 66611483HCID 66611483, compound

Product 1

HCID 66610585HCID 66610585, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)amino)ethanol (Example 225, Step 1; 0.118 g, 0.189 mmol), chloroacetyl chloride (0.023 mL, 0.284 mmol) and triethylamine (0.040 mL, 0.284 mmol) in THF (1 mL) was stirred at ambient temperature for 2 h. 2 M K2CO3 (0.2 mL, aq.) and MeOH (1 mL) were added. After 1 h, water was added to the mixture and it was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give N-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-2-chloro-N-(2-hydroxyethyl)acetamide (0.110 g, 0.157 mmol, 83% yield). m/z (ESI, +ve ion) 699.2 (M+H)+.

Workup

  1. waitAfter 1 h
  2. extractionwas extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-166321a6e0294b158e5ad801017ab6af
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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