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 → N-((1S,2R,3S,4R)-2,3-Dihydroxy-4-{6-[(naphthalen-1-ylmethyl)-amino]-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-cyclopentyl)-propionamide trifluoroacetate

HRID 1697021Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].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.FC(F)(F)C(O)=O.ClC1N=C2C(N=CN2[C@@H]2C[C@H](NC(=O)CC)[C@@H](O)[C@H]2O)=C(N[CH2:79][C:80]2[C:89]3[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=3)[CH:83]=[CH:82][CH:81]=2)N=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:47][C@H:39]1[C@@H:38]([OH:48])[C@H:37]([N:18]2[CH:17]=[N:16][C:15]3[C:19]2=[N:20][C:21]([N:23]2[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]2)=[N:22][C:14]=3[NH:13][CH2:79][C:80]2[C:89]3[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=3)[CH:83]=[CH:82][CH:81]=2)[CH2:41][C@@H:40]1[NH:42][C:43](=[O:46])[CH2:44][CH3:45]

Participants

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 trifluoroacetate

HCID 86622652N-((1S,2R,3S,4R)-4-{2-chloro-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Product 1

HCID 67019363N-((1S,2R,3S,4R)-2,3-Dihydroxy-4-{6-[(naphthalen-1-ylmethyl)-amino]-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-cyclopentyl)-propionamide trifluoroacetate

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 by replacing N-{(1S,2R,3S,4R)-4-[2-chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide with N-((1S,2R,3S,4R)-4-{2-chloro-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate.

Sources & evidence

ORD record: ord-ebb085d79f1842fa9fec0fa71d9a4a76
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163754B2

Reaction notes

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