Sodium Hydroxide → HCID 11627558, compound

HRID 2057072Notes

Reaction equation

HRID 2057072 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1.[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34][NH2:35])([CH3:29])([CH3:28])[CH3:27].[OH-].[Na+].OP([O-])(O)=O.[K+]>C1COCC1.CC#N>[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34][NH:35][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 187201N-BOC-ethylenediamineHCID 516951Monobasic potassium phosphateHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11627558HCID 11627558, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 133 (2.36 g, 6.2 mmol) dissolved in THF (12 ml), was added a solution of N-(2-aminoethyl)carbamic acid tert-butyl ester (163a, 1 ml, 6.2 mmol) in THF (12 ml) followed by addition of 2.5N NaOH (2.5 ml, 6.2 mmol). The reaction mixture was allowed to reflux overnight under nitrogen. The reaction mixture was extracted 3 times with ethyl acetate; combined organic layers were washed with brine solution and dried over potassium carbonate. The filtered sample was concentrated on the rotary evaporator, and the resulting solid was dried overnight under vacuum. Chromatography [Biotage Horizon HPFC system, silica gel, gradient method 0 to 5% CH3OH in CH2Cl2 (over 600 mL)] yielding a white solid (E65, 2.54 mg, 81% yield), mp 94° C.; HPLC: Intertsil ODS-3V C18, 30:70 [(KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 9.7 min, 99.8% purity; MS (TOF MS ES+), m/z 508 (36.5), 506 (M+H, 100).

Workup

  1. temperatureto reflux overnight under nitrogen
  2. extractionThe reaction mixture was extracted 3 times with ethyl acetate
  3. washcombined organic layers were washed with brine solution
  4. dry with materialdried over potassium carbonate
  5. concentrationThe filtered sample was concentrated on the rotary evaporator
  6. customthe resulting solid was dried overnight under vacuum
  7. customChromatography [Biotage Horizon HPFC system, silica gel, gradient method 0 to 5% CH3OH in CH2Cl2 (over 600 mL)] yielding a white solid (E65, 2.54 mg, 81% yield), mp 94° C.

Sources & evidence

ORD record
ord-56c0d7c33f3d46e8bd273c3cbccc3318
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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