Hydrochloric Acid → HCID 71624775, compound

HRID 2422187Notes

Reaction equation

HRID 2422187 reaction equation
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]2[C:13]([NH:14][C@H:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:16][OH:17])=[N:12][C:11]([SH:22])=[N:10][C:9]=2[N:23]=1.[ClH:24]>O.C(#N)C>[Cl:24][C:6]1[S:7][C:8]2[C:13]([NH:14][C@H:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:16][OH:17])=[N:12][C:11]([S:22][S:22][C:11]3[N:12]=[C:13]([NH:14][C@@H:15]([CH2:16][OH:17])[CH2:18][CH:19]([CH3:20])[CH3:21])[C:8]4[S:7][C:6]([Cl:24])=[N:23][C:9]=4[N:10]=3)=[N:10][C:9]=2[N:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178445911HCID 178445911, compound

Product 1

HCID 71624775HCID 71624775, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

Sodium nitrite (5.19 g, 75 mmol) in water (25 mL) was added dropwise at 0° C. to (2R)-2-[[2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol (7.50 g, 25 mmol) in conc. hydrochloric acid (150 mL) and acetonitrile (150 mL). The reaction mixture was stirred for 18 h at 0-5° C., and then poured onto ice (500 mL), and extracted with ethyl acetate. Any remaining solid was filtered off. The combined organic phases were washed sequentially with Brine and saturated aqueous sodium bicarbonate solution. The organic phase was dried and evaporated and the solid previously filtered off was added to this. The total solid was slurried in ethyl acetate, which after filtration provided the title compound (6.3 g, 80% yield).

Workup

  1. additionpoured onto ice (500 mL)
  2. extractionextracted with ethyl acetate
  3. filtrationAny remaining solid was filtered off
  4. washThe combined organic phases were washed sequentially with Brine and saturated aqueous sodium bicarbonate solution
  5. customThe organic phase was dried
  6. customevaporated
  7. filtrationthe solid previously filtered off
  8. additionwas added to this
  9. filtrationwhich after filtration

Sources & evidence

ORD record
ord-427308f5d33f4f1d981e0b9a120de7e4
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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