Hydrochloric Acid → HCID 136359934, compound

HRID 1969907Notes

Reaction equation

HRID 1969907 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[C:8]([C:10]2[C:18]3[N:17]4[CH:19]=[N:20][N:21]=[C:16]4[CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1.[OH-].[Na+].C1C(=O)N(Br)C(=O)C1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[H-].[Na+].COC1C=C([Sn](CCCC)(CCCC)CCCC)C=CN=1>CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]1[N:17]2[C:18]3[C:10]([C:8]4[CH:7]=[CH:6][NH:5][C:4](=[O:3])[CH:9]=4)=[CH:11][NH:12][C:13]=3[N:14]=[CH:15][C:16]2=[N:21][N:20]=1

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 441182272-Methoxy-4-(tributylstannyl)pyridineHCID 136009510HCID 136009510, compound

Product 1

HCID 136359934HCID 136359934, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydrochloric acid (4 M in 1,4-dioxane, 0.300 mL, 1.20 mmol) was added to a slurry of 8-(2-methoxypyridin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.016 g, 0.060 mmol, (prepared using D from Preparation #BBBBB.1 and NaOH, GGG.1 with NBS, K.1 with TsCl and NaH, CCCCC with 2-methoxy-4-(tributylstannyl)pyridine [Synthonix], tetrakis(triphenylphosphinepalladium(0), LiCl, CsF, and CuI, D with NaOH) in EtOH (0.500 mL) and water (0.050 mL). The reaction vessel was sealed and the mixture was warmed to about 80° C. After about 15 h, the mixture was warmed to about 90° C. After about 65 h, the solution was allowed to cool to ambient temperature. The volatiles were removed under reduced pressure to afford 4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-8-yl)pyridin-2(1H)-one (0.0153 g, 94%): LC/MS (Table 1, Method a) Rt=0.73 min; MS m/z 253 (M+H)+.

Workup

  1. custom(prepared
  2. customThe reaction vessel was sealed
  3. temperaturethe mixture was warmed to about 90° C
  4. waitAfter about 65 h
  5. temperatureto cool to ambient temperature
  6. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-9d58f90e97cc459c959dd3fb1ff7fa31
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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