Trifluoroacetic acid → HCID 178508569, compound

HRID 521594Notes

Reaction equation

HRID 521594 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][C:12]3[C:21](I)=[CH:20][C:15]4[O:16][CH2:17][CH2:18][O:19][C:14]=4[CH:13]=3)[NH:8]2)=[C:4]([NH2:23])[N:3]=1.C1C(=O)N(I)C(=O)C1.C(O)(C(F)(F)F)=O>CC#N>[O:16]1[CH2:17][CH2:18][O:19][C:14]2[CH:13]=[C:12]([CH2:11][C:7]3[NH:8][C:9]4[C:5]([N:6]=3)=[C:4]([NH2:23])[N:3]=[C:2]([F:1])[N:10]=4)[CH:21]=[CH:20][C:15]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 178508567HCID 178508567, compound

Product 1

HCID 178508569HCID 178508569, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-fluoro-8-((7-iodo-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-9H-purin-6-amine (S10-5). S10-4 (0.310 g, 1.03 mmol), NIS (0.301 g, 1.34 mmol), CH3CN (20 mL), TFA (2.34 g, 1.56 mL, 20.5 mmol) was stirred at rt overnight. The mixture was dried under reduced pressure and the residue chromatographed (CH2Cl2:MeOH:AcOH, 120:1:0.5 to 90:1:0.5) to give 0.340 g (77%) of a mixture of S10-5 (m/z 428.2 [M+H]+) along with diiodinated compound (m/z 554.1 [M+H]+). LC-MS shows ratio of S10-5 to diiodinated compound to be 83:17. This mixture was not separated but used further in the following step. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 7.37 (s, 1H), 6.82 (s, 1H), 4.25 (s, 4H), 4.18 (s, 2H); MS (ESI) m/z 428.2 [M+H]+.

Workup

  1. customThe mixture was dried under reduced pressure
  2. customthe residue chromatographed (CH2Cl2:MeOH:AcOH, 120:1:0.5 to 90:1:0.5)

Sources & evidence

ORD record
ord-5510a3556b2d4993a865e1ed8fdaa706
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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