Hydrochloric Acid → AZD-8309 (AZD8309)

HRID 1711970Notes

Reaction equation

HRID 1711970 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:12]=[C:13]([NH:27][C@H:28]([CH3:31])[CH2:29][OH:30])[C:14]2[S:19][C:18](=[O:20])[N:17](C3CCCCO3)[C:15]=2[N:16]=1.Cl>C(#N)C.O.O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:12]=[C:13]([NH:27][C@H:28]([CH3:31])[CH2:29][OH:30])[C:14]2[S:19][C:18](=[O:20])[NH:17][C:15]=2[N:16]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59459704HCID 59459704, compound

Product 1

HCID 12073810AZD-8309 (AZD8309)Yield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 5-[[(2,3-difluorophenyl)methyl]thio]-7-[[(1R)-2-hydroxy-1-methylethyl]amino]-3-(tetrahydro-2H-pyran-2-yl)thiazolo[4,5-d]pyrimidin-2-(3H)-one (10.0 g) in acetonitrile (200 ml), water (36 ml) and tetrahydrofuran (30 ml) at 65° C. was added 1M hydrochloric acid (23.25 ml) over 3 hours. The product crystallised during the addition time. The mixture was cooled to 25° C. and the product collected by filtration, washing firstly with water (30 ml) then acetonitrile (30 ml), to afford the title compound as an off-white solid (7.79 g).

Workup

  1. customThe product crystallised during the addition time
  2. filtrationthe product collected by filtration
  3. washwashing firstly with water (30 ml)

Sources & evidence

ORD record
ord-4f6a8f56ca95467eb9e3b571b589b8a4
Source dataset
uspto-grants-2010_09
Patent number
US07790883B2

Reaction notes

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