Thionyl Chloride → HCID 54523477, compound

HRID 1082096Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([NH:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15]O)[C@@H:12]([OH:13])[C@H:10]1[OH:11].S(Br)([Br:29])=O.S(Cl)(Cl)=O>>[Br:29][CH2:15][C@H:14]1[O:17][C@@H:9]([N:8]2[C:18]3[N:19]=[C:2]([Cl:1])[N:3]=[C:4]([NH:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[C:5]=3[N:6]=[CH:7]2)[C@H:10]([OH:11])[C@@H:12]1[OH:13]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 68176Thionyl bromide

HCID 10022940HCID 10022940, compound

Product 1

HCID 54523477HCID 54523477, compoundYield 9%

Procedure

This compound was prepared by general method C, described in more detail in Example 2. 2-Chloro-N-(1-piperidinyl)adenosine [WO 93/08206 (Novo Nordisk A/S)] (3.08 g, 8 mmol) was subjected to the same reaction conditions described above, except that thionyl bromide was substituted for thionyl chloride. The procedure provided the desired 5'-bromo-2-chloro-5'-deoxy-N-(1-piperidinyl)adenosine as a foam (0.19 g, 9%) after column chromatography, 1H-NMR (400 MHz, DMSO-d6) δ1.37 (2H, br, piperidine C--H), 1.62 (4H, m, piperidine C--H), 2.80 (4H, br, piperidine C--H), 3.72, 3.82 (2H, ABX, H-5'a and H-5'b), 4.10 (1H, dt, H-4'), 4.17 (1H, dt, H-3'), 4.68 (1H, q, H-2'), 5.50, 5.62 (1H, 2d, 2'- and 3'-OH), 5.88 (1H, d, H-1'), 8.38 (1H, s, H-8), 9.36 (1H, br, NH). HPLC retention time 11.06 min. (gradient elution over 30 min.; 20-80% acetonitrile/0.1% TFA in water, 96.4% purity at 250 nm). C15H20N6BrClO3.1.3 H2O requires C, 38.2; H, 4.8; N, 17.8. Found: C, 38.7; H, 4.7; N, 17.3%.

Workup

customThis compound was prepared by general method C

Sources & evidence

ORD record: ord-332c3b94134444fc9239141dfb1866d6
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05589467

Reaction notes

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