HCID 66623368, compound → HCID 86622914, compound

HRID 60525Notes

Reaction equation

HRID 60525 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[CH:21]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH2:28])=[O:27])[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@@H:11]([CH2:12][OH:13])[CH2:14][CH:15]([CH3:16])[CH3:17])=[N:8][C:7]([S:18][C@@H:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([NH2:28])=[O:27])[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 66623368HCID 66623368, compoundHCID 178445911HCID 178445911, compound

Product 1

HCID 86622914HCID 86622914, compoundYield 13%

Procedure

The title compound was synthesized as a mixture of two diastereomers by general method A from the reaction of (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (30 mg, 100 μmol) with 3-(1-chloroethyl)benzamide (20 mg, 100 μmol). Separation of the mixture by preparative HPLC gave a single diastereomer (6 mg, 13% yield) as an oil.

Workup

  1. customSeparation of the mixture by preparative HPLC
  2. customgave a single diastereomer (6 mg, 13% yield) as an oil

Sources & evidence

ORD record
ord-a9f2a937b43947468a72ab2cbe7d2731
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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