N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide → {(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(2-{3-[1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ylcarbamoyl)-piperidin-4-yl]-ureido}-ethylcarbamoyl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid tert-butyl ester

HRID 1882587Notes

Reaction equation

[C:1]([O:5][C:6](=[O:60])[NH:7][C@H:8]1[CH2:12][C@@H:11]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][C:16]([C:37](=[O:57])[NH:38][CH2:39][CH2:40][NH:41][C:42]([NH:44][CH:45]2CCN(C4C=CC=CN=4)C[CH2:46]2)=[O:43])=[N:17][C:18]=3[NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:10]([OH:58])[C@@H:9]1[OH:59])([CH3:4])([CH3:3])[CH3:2].[N:61]1([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][N:76]=2)[CH2:66][CH2:65][CH:64]([NH:67][C:68]([N:70]2[CH:74]=[CH:73]N=[CH:71]2)=[O:69])[CH2:63][CH2:62]1.N1(C2C=CC=CN=2)CCC(NC(N2CCC(NC(N3C=CN=C3)=O)CC2)=O)CC1>>[C:1]([O:5][C:6](=[O:60])[NH:7][C@H:8]1[CH2:12][C@@H:11]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][C:16]([C:37](=[O:57])[NH:38][CH2:39][CH2:40][NH:41][C:42]([NH:44][CH:45]2[CH2:46][CH2:71][N:70]([C:68](=[O:69])[NH:67][CH:64]4[CH2:63][CH2:62][N:61]([C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][N:76]=5)[CH2:66][CH2:65]4)[CH2:74][CH2:73]2)=[O:43])=[N:17][C:18]=3[NH:22][CH2:23][CH:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:10]([OH:58])[C@@H:9]1[OH:59])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 3

HCID 21978278N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide

HCID 24863127[(1S,2R,3S,4R)-4-(6-(2,2-Diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-ureido]-ethylcarbamoyl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-carbamic acid tert-butyl ester

HCID 666303144-[(Imidazole-1-carbonyl)-amino]-piperidine-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-amide2×

Product 1

HCID 86647556{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(2-{3-[1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ylcarbamoyl)-piperidin-4-yl]-ureido}-ethylcarbamoyl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid tert-butyl ester

Procedure

The title compound is prepared analogously to [(1S,2R,3S,4R)-4-(6-(2,2-diphenyl-ethylamino)-2-{2-[3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-ureido]-ethylcarbamoyl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-carbamic acid tert-butyl ester (Example 12) by replacing imidazole-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide (Intermediate C) with 4-[(imidazole-1-carbonyl)-amino]-piperidine-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide (Intermediate H).

Sources & evidence

ORD record: ord-4cef6859d4b04480b4a6615fa5c128d9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318750B2

Reaction notes

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