N-((1S,2R,3S,4R)-4-{6-(1-Ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate → Cyclobutanecarboxylic acid ((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-amide

HRID 1697029Notes

Reaction equation

HRID 1697029 reaction equation
F[C:2](F)(F)[C:3](O)=O.C(C([NH:13][C:14]1[N:22]=[C:21]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]([NH:31][C@@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[O:30])[CH2:24]2)[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[C@@H:37]1[CH2:41][C@H:40]([NH:42][C:43](=[O:46])[CH2:44][CH3:45])[C@@H:39]([OH:47])[C@H:38]1[OH:48])CC)C.ClC1N=C2C(N=CN2[C@@H]2C[C@H](NC(C3CCC3)=O)[C@@H](O)[C@H]2O)=C(N[CH2:74][CH:75]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)N=1>>[C:76]1([CH:75]([C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=2)[CH2:74][NH:13][C:14]2[N:22]=[C:21]([N:23]3[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]([NH:31][C@@H:32]4[CH2:36][CH2:35][NH:34][CH2:33]4)=[O:30])[CH2:24]3)[N:20]=[C:19]3[C:15]=2[N:16]=[CH:17][N:18]3[C@@H:37]2[CH2:41][C@H:40]([NH:42][C:43]([CH:44]3[CH2:3][CH2:2][CH2:45]3)=[O:46])[C@@H:39]([OH:47])[C@H:38]2[OH:48])[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1

Participants

3

Reactant 2

HCID 67019376N-((1S,2R,3S,4R)-4-{6-(1-Ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetateHCID 86622641Cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide

Product 1

HCID 67019400Cyclobutanecarboxylic acid ((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-amide

Procedure

This compound is prepared analogously to N-((1S,2R,3S,4R)-4-{6-(1-ethyl-propylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (Example 54) by replacing N-{(1S,2R,3S,4R)-4-[2-chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Example 14) with cyclobutanecarboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide (an intermediate used to prepare Example 23).

Workup

  1. customto prepare Example 23)

Sources & evidence

ORD record
ord-2991d3f201334cd19967c416de77f911
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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