Propionamide → N-((1S,2R,3S,4R)-4-{2-[((S)-1-benzyl-pyrrolidin-3-yl)-methyl-amino]-6-[2-(4-fluoro-phenyl)-2-phenyl-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

HRID 2382459Notes

Reaction equation

HRID 2382459 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@@H:9]1C[CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[C@@H:23]3[CH2:27][C@H:26]([NH:28][C:29](=[O:39])[CH2:30]OCC4C=CC=CC=4)[C@@H:25]([OH:40])[C@H:24]3[OH:41])=[C:16]([NH:42][CH2:43][CH:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49]C=C[CH:46]=3)[N:15]=2)[CH2:10]1.[CH2:57](N1CC[C@H](NC)C1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.F[C:72](F)(F)[C:73](O)=O.Cl[C:79]1N=C2C(N=CN2[C@@H]2C[C@H](NC(=O)CC)[C@@H](O)[C@H]2O)=C(NCC(C2C=CC(F)=CC=2)C2C=CC=CC=2)N=1.C(OC(=O)N([C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)[C@H](O)[C@@H]1O)C(=O)CC)(C)(C)C.C(N)(=O)CC>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:57]([N:8]1[CH2:73][CH2:72][C@H:10]([N:11]([CH3:12])[C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[C@@H:23]3[CH2:27][C@H:26]([NH:28][C:29](=[O:39])[CH2:30][CH3:79])[C@@H:25]([OH:40])[C@H:24]3[OH:41])=[C:16]([NH:42][CH2:43][CH:44]([C:45]3[CH:50]=[CH:49][C:2]([F:7])=[CH:3][CH:46]=3)[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[N:15]=2)[CH2:9]1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

6

Reactant 5

HCID 6578PropionamideHCID 10397666(3S)-1-benzyl-N-methylpyrrolidin-3-amineHCID 44140426[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester2×HCID 66630722N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-acetamide trifluoroacetateHCID 86629557N-((1S,2R,3S,4R)-4-{2-chloro-6-[2-(4-fluoro-phenyl)-2-phenyl-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Product 1

HCID 66631186N-((1S,2R,3S,4R)-4-{2-[((S)-1-benzyl-pyrrolidin-3-yl)-methyl-amino]-6-[2-(4-fluoro-phenyl)-2-phenyl-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Procedure

This compound is prepared analogously to N-{(1S,2R,3S,4R)-4-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-benzyloxy-acetamide trifluoroacetate (Example 1 step 2) by replacing (3R)-3-(Boc-amino)pyrrolidine with ((S)-1-benzyl-pyrrolidin-3-yl)-methyl-amine and by replacing 2-benzyloxy-N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-acetamide with N-((1S,2R,3S,4R)-4-{2-chloro-6-[2-(4-fluoro-phenyl)-2-phenyl-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate [prepared from [(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester (Intermediate G) and the appropriate amine using a procedure analogous to 2R,3S,4R)-4-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 22 steps 1 and 2)]. (MH+ 693.5)

Sources & evidence

ORD record
ord-997b047efe014bdf8cdb10db3b80fbd6
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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