HCID 59186879, compound → HCID 59186880, compound

HRID 1694544Notes

Reaction equation

HRID 1694544 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]=[N:23][CH:24]=[CH:25][C:26]=1[C@H:27](Cl)[CH3:28]>>[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][CH:27]([C:26]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[Cl:20])[CH3:28])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 59186879HCID 59186879, compoundHCID 178445911HCID 178445911, compound

Product 1

HCID 59186880HCID 59186880, compoundYield 8%

Procedure

The title compound was prepared using 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 (860 mg, 2.87 mmol) and 3-chloro-4-[(1R)-1-chloroethyl]pyridine from the previous step. Purification by flash chromatography yielded the title compound (105 mg, 8% yield) as a diastereomeric mixture.

Workup

  1. customThe title compound was prepared
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-caf254a6667c4e60b413833b5a0ec8a5
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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