Triethylamine → HCID 46200667, compound

HRID 1930566Notes

Reaction equation

HRID 1930566 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[CH2:40]([S:42](Cl)(=[O:44])=[O:43])[CH3:41]>CO.ClCCl>[CH2:40]([S:42]([N:21]1[CH2:20][CH2:19][C:17]2[N:18]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([C:5]4[O:1][CH:2]=[N:3][CH:4]=4)=[CH:7][CH:8]=3)[N:14]=[C:15]([N:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:24][CH2:25][OH:26])[C:16]=2[CH2:22]1)(=[O:44])=[O:43])[CH3:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 46200667HCID 46200667, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (100 mg, 0.23 mmol, Example 1) was dissolved in MeOH (0.5 mL) and dichloromethane (5 mL). Triethylamine (0.033 mL, 0.23 mmol) was added followed by ethanesulphonyl chloride (0.022 mL, 0.23 mmol). The reaction mixture was stirred at room temperature for 1 h before the solvent was evaporated under reduced pressure. The crude was dissolved in dimethylformamide and acetonitrile and purified by preparative HPLC yielding 2-((6-(ethylsulfonyl)-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (22.0 mg, 18.11%). MS (ESI) (M+1) m/z 521;

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe crude was dissolved in dimethylformamide
  3. customacetonitrile and purified by preparative HPLC

Sources & evidence

ORD record
ord-6b782054cd394fd9ae83d4df8e2fb67f
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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