Isopropanol → HCID 66649197, compound

HRID 419241Notes

Reaction equation

HRID 419241 reaction equation
Cl[C:2]1[NH:7][C:6]([NH2:21])([NH:8][CH:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH3:10])[N:5]=[CH:4][N:3]=1.C(O[C:27](=[O:45])[CH:28]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)(C)(C)C.[C:46](=O)([O-])[O-].[K+].[K+].[CH:52]([OH:55])([CH3:54])[CH3:53]>>[C:52]([O:55][C:27](=[O:45])[CH:28]([NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][C:4]2[N:3]=[C:2]([NH2:7])[N:21]=[C:6]([NH:8][CH:9]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[CH3:10])[N:5]=2)=[CH:34][CH:35]=1)([CH3:46])([CH3:54])[CH3:53]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 18467918HCID 18467918, compoundHCID 178463647HCID 178463647, compound

Product 1

HCID 66649197HCID 66649197, compoundYield 28%

Procedure

A mixture of 6-chloro-N-(1-naphthalen-2-yl-ethyl)-[1,3,5]triazine-2,2-diamine (90 mg, 0.300 mmol), 2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester (102 mg, 0.303 mmol) and potassium carbonate (82 mg, 0.594 mmol) in isopropanol (8 ml) was refluxed over night. The solvent was removed under reduced pressure and the residue was suspended in ethyl acetate. The solid was filtered and washed with ethyl acetate. The filtrate was concentrated and then redissolved in a mixture of methanol/water (90:10) and purified by a preparative-LC using a Sunfire C18 OBD 100×30 mm ID column (MeOH/H2O/TFA solvent system). The pure fractions were combined and concentrated to give 50 mg of pure product, 3-{4-[4-amino-6-(1-naphthalen-2-yl-ethylamino)-[1,3,5]triazin-2-yloxy]-phenyl}2-tert-butoxycarbonylamino-propionic acid tert-butyl ester, (28% yield).

Workup

  1. temperaturewas refluxed over night
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe solid was filtered
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. dissolutionredissolved in a mixture of methanol/water (90:10)
  7. custompurified by
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bf3b051165494ca28ceb94eb0c3edffa
Source dataset
uspto-grants-2012_01
Patent number
US08093291B2

Reaction notes

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