N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide → 1-(2-Diisopropylamino-ethyl)-3-((R)-1-{9-[(1R,2S,3R,4S)-4-(4-ethyl-pyrazol-1-yl)-2,3-dihydroxy-cyclopentyl]-6-phenethylamino-9H-purin-2-yl}-pyrrolidin-3-yl)-urea

HRID 1641913Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([C@H:8]2[CH2:12][C@@H:11]([N:13]3[CH:21]=[N:20][C:19]4[C:14]3=[N:15][C:16](N[C@@H]3CCNC3)=[N:17][C:18]=4[NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:10]([OH:37])[C@@H:9]2[OH:38])[CH:7]=1)[CH3:2].F[C:40](F)(F)C(O)=O.O[C@@H]1[C@H](O)[C@@H](N2C=C(C)C=N2)C[C@H]1N1C=NC2C1=NC(NC1CCC(NC(NC3CCN(C4C=CC=CN=4)CC3)=O)CC1)=NC=2NCC(C1C=CC=CC=1)C1C=CC=CC=1.[CH:106]([N:109]([CH:120]([CH3:122])[CH3:121])[CH2:110][CH2:111][NH:112][C:113]([N:115]1[CH:119]=[CH:118][N:117]=[CH:116]1)=[O:114])([CH3:108])[CH3:107]>>[CH:106]([N:109]([CH:120]([CH3:122])[CH3:121])[CH2:110][CH2:111][NH:112][C:113]([NH:115][C@@H:119]1[CH2:40][CH2:116][N:117]([C:16]2[N:15]=[C:14]3[C:19]([N:20]=[CH:21][N:13]3[C@@H:11]3[CH2:12][C@H:8]([N:6]4[CH:7]=[C:3]([CH2:1][CH3:2])[CH:4]=[N:5]4)[C@@H:9]([OH:38])[C@H:10]3[OH:37])=[C:18]([NH:22][CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:17]=2)[CH2:118]1)=[O:114])([CH3:108])[CH3:107]

Participants

Reactant 3

HCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide

HCID 66736016(1S,2R,3S,5R)-3-(4-ethyl-pyrazol-1-yl)-5-[6-phenethylamino-2-((R)-pyrrolidin-3-ylamino)-purin-9-yl]-cyclopentane-1,2-diol

HCID 866228111-{4-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(4-methyl-pyrazol-1-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-ylamino]-cyclohexyl}-3-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-urea Trifluoroacetate

Product 1

HCID 667367571-(2-Diisopropylamino-ethyl)-3-((R)-1-{9-[(1R,2S,3R,4S)-4-(4-ethyl-pyrazol-1-yl)-2,3-dihydroxy-cyclopentyl]-6-phenethylamino-9H-purin-2-yl}-pyrrolidin-3-yl)-urea

Procedure

This compound is prepared from (1S,2R,3S,5R)-3-(4-ethyl-pyrazol-1-yl)-5-[6-phenethylamino-2-((R)-pyrrolidin-3-ylamino)-purin-9-yl]-cyclopentane-1,2-diol (Example 55) using a procedure analogous to that of 1-{4-[9-[(1R,2S,3R,4S)-2,3-dihydroxy-4-(4-methyl-pyrazol-1-yl)-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purin-2-ylamino]-cyclohexyl}-3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-urea trifluoroacetate (Example 42) replacing N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide with imidazole-1-carboxylic acid (2-diisopropylamino-ethyl)-amide. MS (ES+) m/e 688 (MH+).

Sources & evidence

ORD record: ord-4796791ab3f846328d4506ea9f732672
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114877B2

Reaction notes

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