4-Fluorobenzylamine → HCID 58296158, compound

HRID 552765Notes

Reaction equation

HRID 552765 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16]C(C)(C)[O:18][C@@H:14]2[C@@H:13]([CH2:21][NH:22][S:23]([NH2:26])(=[O:25])=[O:24])[O:12]1.[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.CCN(C(C)C)C(C)C>CCO>[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[C@@H:11]2[O:12][C@H:13]([CH2:21][NH:22][S:23]([NH2:26])(=[O:24])=[O:25])[C@@H:14]([OH:18])[C@H:15]2[OH:16])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 86607335HCID 86607335, compound

Product 1

HCID 58296158HCID 58296158, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-{[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl}sulfamide (25.0 mg, 0.0618 mmol), 4-fluorobenzylamine (14.1 μL, 0.124 mmol), and DIPEA (10.8 μL, 0.0618 mmol) in EtOH (0.4 mL) was heated at 100° C. for 10 minutes using microwave irradiation. Upon cooling, the mixture was concentrated and the residue dissolved in TFA/water (1 mL, 9:1). The solution was stirred for 10 minutes, concentrated, taken up in MeOH, then concentrated. The residue was purified by reverse phase HPLC to yield 6.5 mg (23%) of final compound.

Workup

  1. custommicrowave irradiation
  2. temperatureUpon cooling
  3. concentrationthe mixture was concentrated
  4. dissolutionthe residue dissolved in TFA/water (1 mL, 9:1)
  5. concentrationconcentrated
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ef7adeb4d0b34aabaa52e82e6e3f5cab
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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