HCID 70798266, compound → HCID 46879420, compound

HRID 1363142Notes

Reaction equation

HRID 1363142 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:3]=1[CH2:4][N:5]1[C:13](=[O:14])[N:12](C(OC(C)(C)C)=O)[C:11]2[C:6]1=[N:7][C:8]([N:22]1[C:26]3[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]1)=[N:9][CH:10]=2>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:37][C:33]1[CH:34]=[CH:35][CH:36]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[C:13](=[O:14])[NH:12][C:11]2[C:6]1=[N:7][C:8]([N:22]1[C:26]3[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]1)=[N:9][CH:10]=2

Participants

3

Reactant 1

HCID 70798266HCID 70798266, compound

Product 1

HCID 46879420HCID 46879420, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 1:1 solution of TFA/DCM (10 mL) was added to tert-Butyl 9-(2,6-difluorobenzyl)-2-(6-cyano-1H-benzo[d]imidazol-1-yl)-8-oxo-8,9-dihydropurine-7-carboxylate (60) and stirred for 1 hr. The solvents were removed en vacuo and the resulting solid was triturated with Et2O, and suspended in 6N HCl. Removal of solvents and trituration with Et2O of the resulting solid gave the titled compound (61) (68 mg) as a HCl salt, MH+=404, 1H NMR (d6-DMSO) δ 11.8 (s, 1H), 9.2 (s, 1H), 8.8 (s, 1H), 8.0 (s, 1H), 7.9 (d, 1H), 7.8 (broad s, 1H), 7.4 (d, 1H), 7.4 (quintet, 1H), 7.1 (m, 2H), 5.2 (s, 2H) ppm, 19F NMR δ −114.3 (m).

Workup

  1. customThe solvents were removed en vacuo
  2. customthe resulting solid was triturated with Et2O
  3. customRemoval of solvents and trituration with Et2O of the resulting solid

Sources & evidence

ORD record
ord-e99970c75fba4159a78ea13229798a65
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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