Benzyl 4-(2-bromoethyl)piperidine-1-carboxylate → phenylmethyl 4-{[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]ethyl}-1-piperidinecarboxylate

HRID 2038173Notes

Reaction equation

HRID 2038173 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:35][CH3:36])[N:6]2[CH2:16][CH2:17][CH2:18][CH:19]1[CH2:24]CCCN1C(OCC1C=CC=CC=1)=O.FC(F)(F)C(O)=O.C(OC1N=C2C(N=C(OC)N2)=C(N)N=1)CCC.BrCCC1CC[N:67]([C:70]([O:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)=[O:71])[CH2:66][CH2:65]1>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:35][CH3:36])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:24][N:67]([C:70]([O:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)=[O:71])[CH2:66][CH2:65]1

Participants

4

Reactant 3

HCID 11056468Benzyl 4-(2-bromoethyl)piperidine-1-carboxylateHCID 58306132Phenylmethyl 2-{3-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]propyl}-1-piperidinecarboxylateHCID 178450370HCID 178450370, compound2×

Product 1

HCID 58306071phenylmethyl 4-{[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]ethyl}-1-piperidinecarboxylate

Procedure

Prepared similarly to Intermediate 11 from 2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetic acid salt (for example, as prepared for Intermediate 6) and phenylmethyl 4-(2-bromoethyl)-1-piperidinecarboxylate (for a preparation, see J. Med. Chem., 2003, 46(13), 2606).

Workup

  1. customfor a preparation

Sources & evidence

ORD record
ord-52bd87fa18fa4d9bbc6707cdd9063da1
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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