Sodium Carbonate → 5-(8-(4-Morpholinophenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)furan-3-carboxamide

HRID 605915Notes

Reaction equation

HRID 605915 reaction equation
C(OC(=O)[N:7]([C:20]1[C:21]2[N:22]([N:34]=[CH:35][N:36]=2)[C:23]([C:26]2[O:27][CH:28]=[C:29]([C:31](=[O:33])[NH2:32])[CH:30]=2)=[CH:24][N:25]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:20]3[C:21]4[N:22]([N:34]=[CH:35][N:36]=4)[C:23]([C:26]4[O:27][CH:28]=[C:29]([C:31]([NH2:32])=[O:33])[CH:30]=4)=[CH:24][N:25]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 67047322[5-(4-Carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 248892905-(8-(4-Morpholinophenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)furan-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [5-(4-carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (33 mg, 0.065 mmol) in a mixture 1:1 DCM:TFA (2 mL) (2 drops of water) is stirred at room temperature for 2 hours. After addition of sat. Na2CO3, a precipitate is formed, collected by filtration and washed with water, diethyl ether and petroleum ether. After drying under vacuum, the title compound is isolated (20 mg, 76%). Conversion into the mesylate salt using 0.1M methanesulfonic acid in MeOH (0.444 mL) yields the title compound (19 mg, 100%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.36 (3H, s, MsOH), 3.22 (4H, m), 3.82-3.89 (4H, m), 7.13 (2H, d), 7.36 (1H, br s), 7.86 (1H, s), 7.95 (3H, m), 8.17 (1H, s), 8.40 (1H, s), 8.84 (1H, s), 10.17 (1H, s). LCMS: Rt 2.60 min (96.9%), m/z (APCI) 406 (M+H)+.

Workup

  1. customa precipitate is formed
  2. filtrationcollected by filtration
  3. washwashed with water, diethyl ether and petroleum ether
  4. customAfter drying under vacuum

Sources & evidence

ORD record
ord-b5c19080150f460f9a2c616dcdcd3ab2
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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