Tetramethyl orthocarbonate → Benzyl (S)-2-(7-methoxy-1H-pyrazolo[3,4-e]benzoxazol-1-yl)-1-methylethylcarbamate

HRID 1247009Notes

Reaction equation

HRID 1247009 reaction equation
[NH2:1][C:2]1[C:3]([OH:25])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13])[N:8]=[CH:7]2.[C:26](OC)(OC)(OC)[O:27][CH3:28].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:26][O:27][C:28]1[O:25][C:3]2[CH:4]=[CH:5][C:6]3[CH:7]=[N:8][N:9]([CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH3:13])[C:10]=3[C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 74613Tetramethyl orthocarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 136335132Benzyl (S)-2-(7-amino-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

Product 1

HCID 86604076Benzyl (S)-2-(7-methoxy-1H-pyrazolo[3,4-e]benzoxazol-1-yl)-1-methylethylcarbamate

Procedure

The product from Step D (0.47 g) was combined with tetramethyl orthocarbonate (15 mL), p-toluenesulfonic acid hydrate (10 mg) and the mixture was stirred at room temperature for 1 h. The reaction was quenched with triethylamine (1 ml) and the reaction mixture was evaporated to a residue which was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give a colorless oil (60 mg): LC/MS m/z 381.

Workup

  1. customThe reaction was quenched with triethylamine (1 ml)
  2. customthe reaction mixture was evaporated to a residue which
  3. customwas purified by chromatography (silica gel, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-a1023c884b4043c2b58a0d345b229a02
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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