Dimethylformamide → N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-(dimethylamino)adenosine

HRID 375153Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C@H:12]([NH:14][C:15]1[C:16]2[N:17]=[CH:18][N:19]([C:29]=2[N:30]=[C:31](Cl)[N:32]=1)[C@@H:20]1[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]1[OH:22])[CH3:13].[CH3:34][N:35](C)[CH:36]=O>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C@H:12]([NH:14][C:15]1[C:16]2[N:17]=[CH:18][N:19]([C:29]=2[N:30]=[C:31]([N:35]([CH3:36])[CH3:34])[N:32]=1)[C@@H:20]1[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]1[OH:22])[CH3:13]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 9936084Nnc-21-0136

Product 1

HCID 9914564N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-(dimethylamino)adenosineYield 12%

Procedure

The title compound was prepared according to general method B by reaction of N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-chloroadenosine (1.02 g, 2.0 mmol) (Example 5)in dimethylformamide (10 ml) to provide the desired N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-(dimethylamino )adenosine (0.12 g, 12%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 2.92 (6H, s, --N(CH3)2), 3.40-3.72 (4H, m, H-5'a and H-5'b and --CH2 --), 3.88 (1H, q, H-4'), 4.15 (1H, q, H-3'), 4.65 (1H, q, H-2'), 4.72-4.85 (1H, m, --CH--), 4.89 (1H, t, 5'-OH), 5.14, 5.36 (2H, 2d, 2'- and 3'-OH), 5.75 (1H, d, H- 1'), 7.35, 7.46 (2H, 2 t, Ar-H), 7.50 (1H, d, N--H), 7.84, 7.99 (2H, 2d, Ar-H), 7.94 (1H, s, H-8). HPLC retention time 16.8 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-d9ca1352f91c4fe683448198516f0d8a
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484774

Reaction notes

Loading…