Hydrochloric Acid → HCID 66547916, compound

HRID 1186466Notes

Reaction equation

HRID 1186466 reaction equation
C(OC(=O)[N:7]([CH:27]([CH3:29])[CH3:28])[C:8]1[C:9]2[N:10]([C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](S(C)(=O)=O)[N:18]=3)=[CH:15][N:16]=2)[CH:11]=[CH:12][N:13]=1)(C)(C)C.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>C(O)CCC>[CH:27]([NH:7][C:8]1[C:9]2[N:10]([C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:18]=3)=[CH:15][N:16]=2)[CH:11]=[CH:12][N:13]=1)([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 68226920HCID 68226920, compound

Product 1

HCID 66547916HCID 66547916, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To isopropyl-[3-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester (117 mg, 0.27 mmol) (from Example 11 supra) was added aniline (38 μL, 0.42 mmol) in nBuOH (3 mL) followed by conc.HCl (38 μL, 0.46 mmol) and the reaction was shaken at 95° C. overnight. After this time the reaction was concentrated to dryness, dissolved in DMSO (1.8 mL) and then purified by preparative HPLC to give isopropyl-[3-(2-phenylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine. (Yield 27.3 mg, 29%). LC-MS: [M+H]+ 346.3.

Workup

  1. concentrationAfter this time the reaction was concentrated to dryness
  2. dissolutiondissolved in DMSO (1.8 mL)
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4f9c41ff8c37440f91d6b8b55828b1f0
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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