Water → HCID 178485113, compound

HRID 1926169Notes

Reaction equation

HRID 1926169 reaction equation
[CH3:1][N:2](C(OC(C)(C)C)=O)[C:3](N1C=CC=N1)=[N:4]C(OC(C)(C)C)=O.C(N(C(C)C)C(C)C)C.[ClH:33].Cl.[NH2:35][CH2:36][CH2:37][N:38]1[C:46]2[C:45]([NH:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][C:55]4[CH:60]=[CH:59][CH:58]=[C:57]([C:61]([F:64])([F:63])[F:62])[CH:56]=4)=[C:50]([Cl:65])[CH:49]=3)=[N:44][CH:43]=[N:42][C:41]=2[CH:40]=[CH:39]1.O>C(#N)C>[ClH:65].[ClH:33].[Cl:65][C:50]1[CH:49]=[C:48]([NH:47][C:45]2[C:46]3[N:38]([CH2:37][CH2:36][NH:35][C:3]([NH:2][CH3:1])=[NH:4])[CH:39]=[CH:40][C:41]=3[N:42]=[CH:43][N:44]=2)[CH:53]=[CH:52][C:51]=1[O:54][C:55]1[CH:60]=[CH:59][CH:58]=[C:57]([C:61]([F:64])([F:63])[F:62])[CH:56]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 568513565-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochlorideHCID 66662001HCID 66662001, compound

Product 1

HCID 178485113HCID 178485113, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methyl-N,N′-bis(tert-butoxy carbonyl)-1H-pyrazole-1-carboxamidine (138 mg) and ethyldiisopropylamine (0.16 mL) in acetonitrile (4 mL) was added 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (200 mg), and the mixture was stirred at room temperature for 4 days. Under ice-cooling, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=80:20→100:0). The obtained product was dissolved in ethyl acetate, 4N hydrochloric acid/ethyl acetate was added, and the mixture was stirred at room temperature for 22 hrs. The precipitate was collected by filtration, and washed with ethyl acetate and diisopropyl ether to give the title compound (98 mg) as a powder.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=80:20→100:0)
  7. dissolutionThe obtained product was dissolved in ethyl acetate
  8. addition4N hydrochloric acid/ethyl acetate was added
  9. stirringthe mixture was stirred at room temperature for 22 hrs
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-cb95d733db4646c6939544cf9e7a050a
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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