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

HRID 1697026Notes

Reaction equation

HRID 1697026 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C@H:9]1[C@@H:13]([OH:14])[C@H:12]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([NH:36][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)=[N:19][C:20]=3[NH:24][CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)[CH2:11][C@@H:10]1[NH:45][C:46](=[O:49])[CH2:47][CH3:48].[N:50]1([CH2:56][CH2:57][NH2:58])[CH2:55][CH2:54][CH2:53]CC1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:50][CH:55]1[CH2:2][CH2:38][CH:37]([NH:36][C:18]2[N:17]=[C:16]3[C:21]([N:22]=[CH:23][N:15]3[C@@H:12]3[CH2:11][C@H:10]([NH:45][C:46](=[O:49])[CH2:47][CH3:48])[C@@H:9]([OH:8])[C@H:13]3[OH:14])=[C:20]([NH:24][CH2:25][C:26]3[C:35]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:29]=[CH:28][CH:27]=3)[N:19]=2)[CH2:53][CH2:54]1.[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C@H:9]1[C@@H:13]([OH:14])[C@H:12]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([NH:36][CH2:37][CH2:38][C:56]2[N:50]=[CH:55][NH:58][CH:57]=2)=[N:19][C:20]=3[NH:24][CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)[CH2:11][C@@H:10]1[NH:45][C:46](=[O:49])[CH2:47][CH3:48].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:44]([N:39]1[CH2:40][CH2:41][CH2:42][C@@H:38]1[CH2:37][NH:36][C:18]1[N:17]=[C:16]2[C:21]([N:22]=[CH:23][N:15]2[C@@H:12]2[CH2:11][C@H:10]([NH:45][C:46](=[O:49])[CH2:47][CH3:48])[C@@H:9]([OH:8])[C@H:13]2[OH:14])=[C:20]([NH:24][CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)[N:19]=1)[CH3:43]

Participants

5

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 67019398N-{(1S,2R,3S,4R)-2,3-Dihydroxy-4-[6-[(naphthalen-1-ylmethyl)-amino]-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-cyclopentyl}-propionamide trifluoroacetate

Product 3

HCID 67019319N-((1S,2R,3S,4R)-4-{2-[((R)-1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetateHCID 67019392N-((1S,2R,3S,4R)-4-{2-(4-amino-cyclohexylamino)-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl)-2,3-dihydroxy-cyclopentyl}-propionamide trifluoroacetateHCID 178460283HCID 178460283, compound

Procedure

These compounds namely, N-((1S,2R,3S,4R)-4-{2-(4-amino-cyclohexylamino)-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (Example 67), N-((1S,2R,3S,4R)-2,3-dihydroxy-4-{2-[2-(1H-imidazol-4-yl)-ethylamino]-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-cyclo pentyl)-propionamide trifluoroacetate (Example 68) and N-((1S,2R,3S,4R)-4-{2-[((R)-1-Ethyl-pyrrolidin-2-ylmethyl)-amino]-6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (Example 69) are prepared analogously to N-{(1S,2R,3S,4R)-2,3-dihydroxy-4-[6-[(naphthalen-1-ylmethyl)-amino]-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-cyclopentyl}-propionamide trifluoroacetate (Example 66) by replacing 2-piperidin-1-yl-ethylamine with the appropriate amine.

Sources & evidence

ORD record
ord-c723fbc468534fb58c84f241103abb9f
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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