Dimethylformamide → HCID 59497020, compound

HRID 655128Notes

Reaction equation

HRID 655128 reaction equation
[OH:1][C@@H:2]1[CH:6]([OH:7])[CH:5]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[O:4][C@H:3]1[N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([N:37]1[CH2:41][CH2:40][C@@H:39]([NH:42][C:43]([NH:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[O:44])[CH2:38]1)=[N:17][C:18]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:52](=[O:55])([O-])[O-].[K+].[K+].[CH3:58]N(C=O)C>>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([C:8]2[N:12]=[N:11][N:10]([CH2:58][CH2:52][OH:55])[N:9]=2)[O:4][C@H:3]1[N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([N:37]1[CH2:41][CH2:40][C@@H:39]([NH:42][C:43]([NH:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[O:44])[CH2:38]1)=[N:17][C:18]=2[NH:22][CH2:23][CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67541675HCID 67541675, compound

Product 1

HCID 59497020HCID 59497020, compound

Procedure

A solution of 1-{(R)-1-[9-[(2R,3R,4S R)-3,4-dihydroxy-5-(2H-tetrazol-5-yl)-tetrahydro-furan-2-yl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea in DMF is treated with potassium carbonate followed by 3-bromoethanol and stirred at RT for 18 hours. The mixture is then filtered and the filtrate is concentrated in vacuo. Purification of the crude product by C-18 reverse phase column chromatography eluting with acetonitrile:water (0.1% TFA) (gradient 0-100% acetonitrile) to affords the titled compound.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customPurification of the crude product by C-18 reverse phase column chromatography
  4. washeluting with acetonitrile

Sources & evidence

ORD record
ord-ec0ae89cfd5342b1acb90abbd8a5df18
Source dataset
uspto-grants-2011_12
Patent number
US08071565B2

Reaction notes

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