Cyclopentylamine → HCID 59107264, compound

HRID 966396Notes

Reaction equation

[H][H].[CH:3]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9]([C:13]1[CH:48]=[CH:47][C:16]([CH2:17][O:18][C:19]2[N:27]=[C:26]3[C:22]([N:23]=[CH:24][N:25]3[C@@H:28]3[O:40][C@H:39]([CH2:41][O:42]C(=O)C)[C@@H:34]([O:35]C(=O)C)[C@H:29]3[O:30]C(=O)C)=[C:21](Cl)[N:20]=2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>>[C:9]([C:13]1[CH:48]=[CH:47][C:16]([CH2:17][O:18][C:19]2[N:20]=[C:21]([NH:8][CH:3]3[CH2:7][CH2:6][CH2:5][CH2:4]3)[C:22]3[N:23]=[CH:24][N:25]([C:26]=3[N:27]=2)[C@@H:28]2[O:40][C@H:39]([CH2:41][OH:42])[C@@H:34]([OH:35])[C@H:29]2[OH:30])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Reactant 3

HCID 2906Cyclopentylamine

HCID 59107267HCID 59107267, compound

HCID 178418361HCID 178418361, compound

Product 1

HCID 59107264HCID 59107264, compoundYield 50%

Procedure

A compound having a structure of the above formula was prepared where the substituent R1 is cyclopentyl, R2 is hydrogen, and R3 is —CH2(4-(C(CH3)3)C6H4 (4-tert-butylbenzoyl). The compound (C25H35N5O5) was prepared by reaction of cyclopentylamine with 2-[4-(tert-butyl)benzyloxy]-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 8) as described in Example 2, Step E. The final product was isolated in 50% yield as a solid with a melting point of 118-120° C. 1H-NMR (CDCl3): 1.3 (s, 9H); 1.6 (m, 6H); 2.0 (m, 2H); 3.46 (m, 3H); 3.75 (m, 1H); 3.89 (m, 1H); 4.28 (s, 1H); 4.42 (m, 2H); 5.1 (m, 1H); 5.29 (s, 2H); 5.7 (d, 1H); 5.7 (m, 1H); 7.35 (s, 4H); 7.57 (bs, 1H).

Workup

customwas prepared where the substituent R1

Sources & evidence

ORD record: ord-e2e5dc5ac29744149f5477f19764a16f
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951932B2

Reaction notes

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