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

HRID 2292603Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:20][C@H:21]([CH3:33])[CH2:22][S:23][C:24]2[S:25][C:26]3[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=3[N:28]=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][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH3:34][N:35](C)[CH:36]=O>>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[S:23][CH2:22][C@H:21]([NH:20][C:4]1[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=[C:2]([N:35]([CH3:36])[CH3:34])[N:3]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])[CH3:33]

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 (DMSO6) δ1.38 (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-27e406ce8ede48fe8bc3548965430a74
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05683989

Reaction notes

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