Chlorine → HCID 178509501, compound

HRID 2074199Notes

Reaction equation

HRID 2074199 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[C@H:22]1[CH2:27][CH2:26][C@H:25]([O:28]C)[CH2:24][CH2:23]1.ClCl.[F:33][C:34]1([F:38])[CH2:37][NH:36][CH2:35]1>ClC1C2C(=NC(=O)N=1)N=CN=2>[F:33][C:34]1([F:38])[CH2:37][N:36]([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[C@H:22]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]2)[CH2:35]1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 27582483,3-DifluoroazetidineHCID 178496593HCID 178496593, compound

Product 1

HCID 178509501HCID 178509501, compound

Reagents, catalysts & solvents 1

HCID 67059519HCID 67059519, compoundSolvent

Procedure

Synthesized from 3-(6-chloro-9-(trans-4-methoxycyclohexyl)-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile by demethylation, followed by displacement of chlorine in the 6-chloropurinone with 3,3-difluoroazetidine. 1HNMR (300 MHz, CDCl3+CD3OD) δ, ppm: 9.12 (s, 1H), 8.92 (s, 1H), 7.90 (d, 1H), 7.64 (dd, 1H), 4.71 (t, 4H), 4.46-4.32 (m, 1H), 3.98-3.83 (m, 1H), 2.64-2.46 (m, 2H), 2.24-2.15 (m, 2H), 1.97-1.87 (m, 2H), 1.62-1.46 (m, 2H); MS (EI) m/z 467.0 (MH)+.

Sources & evidence

ORD record
ord-976acdcb055e4af2b16cd2c9fe5f92df
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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