Lithium Hydroxide → 4-(3-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid trifluoroacetate

HRID 1641927Notes

Reaction equation

HRID 1641927 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([O:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26]([NH:28][C@@H:29]3[CH2:33][CH2:32][N:31]([C:34]4[N:42]=[C:41]5[C:37]([N:38]=[CH:39][N:40]5[C@@H:43]5[CH2:47][C@H:46]([N:48]6[CH:52]=[C:51]([CH2:53][OH:54])[CH:50]=[N:49]6)[C@@H:45]([OH:55])[C@H:44]5[OH:56])=[C:36]([NH:57][CH2:58][CH:59]([C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)[C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)[N:35]=4)[CH2:30]3)=[O:27])[CH2:21][CH2:20]2)=[N:17][CH:18]=1)=[O:12])C.[OH-].[Li+]>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:56][C@@H:44]1[C@H:45]([OH:55])[C@@H:46]([N:48]2[CH:52]=[C:51]([CH2:53][OH:54])[CH:50]=[N:49]2)[CH2:47][C@H:43]1[N:40]1[CH:39]=[N:38][C:37]2[C:41]1=[N:42][C:34]([N:31]1[CH2:32][CH2:33][C@@H:29]([NH:28][C:26](=[O:27])[NH:25][CH:22]3[CH2:21][CH2:20][N:19]([C:16]4[CH:15]=[CH:14][C:13]([C:11]([OH:12])=[O:10])=[CH:18][N:17]=4)[CH2:24][CH2:23]3)[CH2:30]1)=[N:35][C:36]=2[NH:57][CH2:58][CH:59]([C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 866228134-(3-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentyl]-6 (2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid ethyl ester trifluoroacetate

Product 1

HCID 866228234-(3-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-dihydroxy-4-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid ethyl ester trifluoroacetate (Example 79) (23 mg, 0.023 mmol) is dissolved in methanol (2 ml). Aqueous lithium hydroxide (6 mg, 0.23 mmol) is added and the reaction mixture is stirred at room temperature for 18 hours. The solvent is removed in vacuo. The title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% MeCN in water—0.1% TFA). MS (ES+) m/e 422 (MH+/2).

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-983621b176d64e56ad2b5049686624df
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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