5-Chloro-2-[(1R)-1-chloroethyl]pyridine → HCID 24762208, compound

HRID 2422175Notes

Reaction equation

HRID 2422175 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:20][C:21]1[CH:22]=[CH:23][C:24]([C@H:27](Cl)[CH3:28])=[N:25][CH:26]=1>>[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:27]([C:24]3[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=3)[CH3:28])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 598688305-Chloro-2-[(1R)-1-chloroethyl]pyridineHCID 178445911HCID 178445911, compound

Product 1

HCID 24762208HCID 24762208, compoundYield 30%

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 (823 mg, 2.75 mmol) and 5-chloro-2-[(1R)-1-chloroethyl]pyridine (<4.4 mmol). Purification by flash column chromatography (eluent DCM: methanol gradient) yielded 350 mg (30% yield) of the title compound.

Workup

  1. customPurification by flash column chromatography (eluent DCM: methanol gradient)

Sources & evidence

ORD record
ord-e324b5e86de94b97931c07c013b0dbac
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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