Methyl Isocyanate → N-[(5-{6[((3R)oxolan-3yl)amino]purin-9-yl}(3S,2R,4R,5R)3,4-dihydroxyoxolan-2-yl)methyl](cyclopentylamino)carboxamide

HRID 1368856Notes

Reaction equation

HRID 1368856 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@@H:16]2[O:20][C@H:19]([CH2:21][NH:22][C:23]([NH:25][CH3:26])=[O:24])[C@@H:18]([OH:27])[C@H:17]2[OH:28])[CH2:2]1.[CH:29]1(N=C=O)[CH2:33]C[CH2:31][CH2:30]1.CN=C=O>>[O:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@@H:16]2[O:20][C@H:19]([CH2:21][NH:22][C:23]([NH:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:33]3)=[O:24])[C@@H:18]([OH:27])[C@H:17]2[OH:28])[CH2:2]1

Participants

4

Reactant 3

HCID 12228Methyl IsocyanateHCID 643500Cyclopentyl IsocyanateHCID 20592071n-[(5-{6-[((3r)Oxolan-3-yl)amino]purin-9-yl}(3s,2r,4r,5r)-3,4-dihydroxyoxolan-2-yl)methyl](methylamino)carboxamide

Product 1

HCID 20592068N-[(5-{6[((3R)oxolan-3yl)amino]purin-9-yl}(3S,2R,4R,5R)3,4-dihydroxyoxolan-2-yl)methyl](cyclopentylamino)carboxamide

Procedure

Compound 76 was prepared in the manner of compound 24 substituting cyclopentyl isocyanate for methyl isocyanate and refluxing for 16 h [MS 448.3 (M+1)].

Workup

  1. temperaturerefluxing for 16 h [MS 448.3 (M+1)]

Sources & evidence

ORD record
ord-2c15847345524b30a9e7e2f6435309b7
Source dataset
uspto-grants-2003_06
Patent number
US06576620B2

Reaction notes

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