1-Amino-2-propanol → HCID 58886645, compound

HRID 1766795Notes

Reaction equation

HRID 1766795 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].C(N(CC)CC)C.[C:13]([O:17][C:18](=[O:36])[C:19]1[C:24]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=2[Cl:33])=[C:23]([Cl:34])[C:22](Cl)=[N:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>C(#N)C.CCOC(C)=O>[C:13]([O:17][C:18](=[O:36])[C:19]1[C:24]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=2[Cl:33])=[C:23]([Cl:34])[C:22]([NH:1][CH2:2][CH:3]([OH:5])[CH3:4])=[N:21][CH:20]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 8471TriethylamineHCID 58886663HCID 58886663, compound

Product 1

HCID 58886645HCID 58886645, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Amino-propan-2-ol (2.44 g, 30.3 mmol) and triethylamine (0.42 mL, 3.03 mmol) were added to a solution of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloro-nicotinic acid tert-butyl ester (1.37 g, 3.03 mmol) in acetonitrile (30 mL). The reaction was heated to reflux. After 23 hours the reaction was cooled to room temperature and diluted with EtOAc, washed with saturated NaHCO3, water, brine, dried over Na2SO4 and concentrated to a white solid. Purification by flash column chromatography (20:1 dichloromethane/methanol) provided the desired product as a white solid (1.11 g, 75%). MS APCI (+) m/z 492, 494 (M+, Cl, Br pattern) detected.

Workup

  1. temperatureThe reaction was heated to reflux
  2. washwashed with saturated NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a white solid
  5. customPurification by flash column chromatography (20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-0f128f1a11bb4b40875b3e6f94498722
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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