2-((R)-1-chloro-ethyl)-isonicotinonitrile → 2-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}isonicotinonitrile

HRID 1694557Notes

Reaction equation

HRID 1694557 reaction equation
Cl[C@@H:2]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])[CH3:3].[NH2:12][C:13]1[S:14][C:15]2[C:20]([NH:21][C@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24])=[N:19][C:18]([SH:29])=[N:17][C:16]=2[N:30]=1>>[NH2:12][C:13]1[S:14][C:15]2[C:20]([NH:21][C@@H:22]([CH2:23][OH:24])[CH2:25][CH:26]([CH3:27])[CH3:28])=[N:19][C:18]([S:29][C@H:2]([C:4]3[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=3)[C:7]#[N:8])[CH3:3])=[N:17][C:16]=2[N:30]=1

Participants

3

Reactant 2

HCID 598688402-((R)-1-chloro-ethyl)-isonicotinonitrileHCID 178445911HCID 178445911, compound

Product 1

HCID 591868822-{(1S)-1-[(2-Amino-7-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)thio]ethyl}isonicotinonitrileYield 20.2%

Procedure

The title compound was prepared according to General Method A starting from 2-((R)-1-chloro-ethyl)-isonicotinonitrile (46 mg, 0.28 mmol) and (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (69 mg, 0.23 mmol). Purification by chiral HPLC (Column: Chiralpak AD 50×150 mm, eluent: heptane:isopropanol 85:15), flowrate 60 ml/min) yielded the title compound (20 mg, 20% yield).

Workup

  1. customThe title compound was prepared
  2. customPurification by chiral HPLC (Column: Chiralpak AD 50×150 mm, eluent: heptane:isopropanol 85:15), flowrate 60 ml/min)

Sources & evidence

ORD record
ord-3aea12f660ae42a595950e40397af94a
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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