Hydrochloric Acid → (+/-)-2-[[2-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-3-methoxy-1-propanol

HRID 1097370Notes

Reaction equation

HRID 1097370 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([NH:10][CH:11]([CH2:14][O:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])=[N:6][C:5]=2[N:27]=1.[ClH:28].N([O-])=O.[Na+]>O>[Cl:28][C:2]1[S:3][C:4]2[C:9]([NH:10][CH:11]([CH2:14][O:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])=[N:6][C:5]=2[N:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 86635806(+/-)-2-[[2-Amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-3-methoxy-1-propanol

Product 1

HCID 86635807(+/-)-2-[[2-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-3-methoxy-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of the product from example 40 step b) (1.0 g) in a mixture of concentrated hydrochloric acid (40 ml) and water (32 ml) cooled in ice water was added a solution of sodium nitrite (0.4 g) in water (5 mL), stirred at this temp for 2 hours. The mixture was then extracted into ethyl acetate, dried and evaporated to give the subtitle compound, (0.6 g).

Workup

  1. extractionThe mixture was then extracted into ethyl acetate
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-85c4acaa6cac466fac7677565637ccea
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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