Hydrochloric Acid → HCID 86625795, compound

HRID 2422191Notes

Reaction equation

HRID 2422191 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:17])=[N:6][C:5]=2[N:18]=1.[ClH:19].N([O-])=O.[Na+]>C(#N)C.O>[Cl:19][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:17][S:17][C:7]3[N:8]=[C:9]([NH:10][C@@H:11]([CH2:12][OH:13])[CH2:14][CH2:15][CH3:16])[C:4]4[S:3][C:2]([Cl:19])=[N:18][C:5]=4[N:6]=3)=[N:6][C:5]=2[N:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178448295HCID 178448295, compound

Product 1

HCID 86625795HCID 86625795, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(2R)-2-[(2-Amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]pentan-1-ol (4.0 g, 14 mmol) was dissolved in acetonitrile (100 ml) and concentrated hydrochloric acid (150 mL). Sodium nitrite (1.93 g, 28 mmol) was dissolved in water (10 mL) and added at 0° C. The reaction mixture was left at 0° C. for 2 days until the reaction was complete by LCMS. The reaction mixture was poured onto ice and the precipitated product was collected by filtration. The solid was dried in vacuo to give 3.3 g (78% yield) of the title compound.

Workup

  1. additionadded at 0° C
  2. additionThe reaction mixture was poured onto ice
  3. filtrationthe precipitated product was collected by filtration
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-d2e50841e782430bad3149d05bfba6a6
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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