N-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(5-methyl-tetrazol-2-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-methanesulfonamide → N-((R)-1-{6-(2,2-Diphenyl-ethylamino)-9-[(1R,2S,3R,4S)-4-(5-ethyl-tetrazol-2-yl)-2,3-dihydroxy-cyclopentyl]-9H-purin-2-yl}-pyrrolidin-3-yl)-methanesulfonamide

HRID 1641912Notes

Reaction equation

HRID 1641912 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([N:8]2[N:12]=[N:11][C:10]([CH3:13])=[N:9]2)[CH2:4][C@H:3]1[N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([N:38]1[CH2:42][CH2:41][C@@H:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:39]1)=[N:18][C:19]=2[NH:23][CH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N[C@@H:49]1CCN(C2N=C3C(N=CN3[C@@H]3C[C@H](N4N=NC(CC)=N4)[C@@H](O)[C@H]3O)=C(NCC(C3C=CC=CC=3)C3C=CC=CC=3)N=2)C1>>[C:26]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][NH:23][C:19]2[N:18]=[C:17]([N:38]3[CH2:42][CH2:41][C@@H:40]([NH:43][S:44]([CH3:47])(=[O:45])=[O:46])[CH2:39]3)[N:16]=[C:15]3[C:20]=2[N:21]=[CH:22][N:14]3[C@@H:3]2[CH2:4][C@H:5]([N:8]3[N:12]=[N:11][C:10]([CH2:13][CH3:49])=[N:9]3)[C@@H:6]([OH:7])[C@H:2]2[OH:1])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 11614437N-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(5-methyl-tetrazol-2-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-methanesulfonamideHCID 11650095(1R,2S,3R,5S)-3-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol

Product 1

HCID 11621684N-((R)-1-{6-(2,2-Diphenyl-ethylamino)-9-[(1R,2S,3R,4S)-4-(5-ethyl-tetrazol-2-yl)-2,3-dihydroxy-cyclopentyl]-9H-purin-2-yl}-pyrrolidin-3-yl)-methanesulfonamide

Procedure

The title compound is prepared using a procedure analogous to that of N-{(R)-1-[9-[(1R,2S,3R,4S)-2,3-dihydroxy-4-(5-methyl-tetrazol-2-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-methanesulfonamide (Example 67) by replacing (1R,2S,3R,5S)-3-[6-(2,2-diphenyl-ethylamino)-2-((R)-pyrrolidin-3-ylamino)-purin-9-yl]-5-(5-methyl-tetrazol-2-yl)-cyclopentane-1,2-diol trifluoroacetate (Example 7) with (1R,2S,3R,5S)-3-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol (Example 48). MS (ES+) m/e 674 (MH+).

Sources & evidence

ORD record
ord-9ecca1dd622242ebb13ce7a89a597275
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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