2-[(1R)-1-Chloroethyl]-5-fluoropyridine → HCID 25064754, compound

HRID 1694543Notes

Reaction equation

HRID 1694543 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][C@H:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 598688392-[(1R)-1-Chloroethyl]-5-fluoropyridineHCID 178445911HCID 178445911, compound

Product 1

HCID 25064754HCID 25064754, compoundYield 18%

Procedure

The title compound was prepared by General method A starting from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (550 mg, 1.8 mmol) and 2-[(1R)-1-chloroethyl]-5-fluoropyridine (0.46 g, 2.9 mmol). The product was purified by flash column chromatography followed by preparative HPLC (Column: Reprosil, eluent isopropanol:heptane 20:80, flow: 16 mL/min) collecting the first eluting isomer, to yield 135 mg (18% yield) of the title compound.

Workup

  1. customThe product was purified by flash column chromatography
  2. customcollecting the first eluting isomer

Sources & evidence

ORD record
ord-06ff99d0fe2249e5bbd058074c2a38d2
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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