3,3-Difluoroazetidine hydrochloride → 3-(6-(3,3-difluoroazetidin-1-yl)-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

HRID 2074193Notes

Reaction equation

HRID 2074193 reaction equation
Cl[C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:30])[N:6]2[CH:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH3:23].Cl.[F:32][C:33]1([F:37])[CH2:36][NH:35][CH2:34]1>>[F:32][C:33]1([F:37])[CH2:36][N:35]([C:2]2[N:10]=[C:9]([N:11]3[C:15]4[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[N:8]=[C:7]3[C:3]=2[NH:4][C:5](=[O:30])[N:6]3[CH:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH3:23])[CH2:34]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 576127403-(6-chloro-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

Product 1

HCID 576126963-(6-(3,3-difluoroazetidin-1-yl)-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrileYield 57%

Procedure

White semi-solid. 57% yield. Synthesized from 3-(6-chloro-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile (19 mg, 0.046 mmol) and 3,3-difluoroazetidine hydrochloride (3 equiv.) following the general procedure for displacement reactions of 6-chloropurinones with aliphatic amines. 1H NMR (300 MHz, CD3OD) δ, ppm: 9.27 (s, 1H), 9.20-9.00 (br m, 1H), 8.78 (d, 1H), 8.88-8.77 (m, 1H, overlapping with 8.78 ppm), 8.63 (s, 1H), 8.09 (br s, 1H), 7.88 (d, 1H), 7.67 (d, 1H), 6.13 (q, J=7.1 Hz, 1H), 4.78 (t, 4H), 2.16 (d, J=7.1 Hz, 3H); MS (EI) m/z 474.0 (MH)+.

Sources & evidence

ORD record
ord-4f35ffe816ee45a293a34e4457c6ee48
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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