Ethyl orthoformate → HCID 44132886, compound

HRID 1916270Notes

Reaction equation

HRID 1916270 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[O:27][CH:28]=2)[N:3]=1.C(O[CH2:44][CH3:45])(OCC)OCC.C([O-])(=O)C.[NH4+:50]>>[NH2:9][C:8]1[C:7]2[C:6]([C:10]3[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=3)=[C:5]([C:20]#[N:21])[C:4]([S:22][CH2:23][C:24]3[N:25]=[C:26]([C:29]4[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=4)[O:27][CH:28]=3)=[N:3][C:2]=2[N:1]=[C:44]([CH3:45])[N:50]=1

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 517165Ammonium AcetateHCID 25205590HCID 25205590, compound

Product 1

HCID 44132886HCID 44132886, compound

Procedure

50 mg (0.10 mmol) of the compound from Example 15A, 113 mg (0.69 mmol) of triethyl orthoformate and 38 mg (0.50 mmol) of ammonium acetate were combined and reacted in a microwave at 160° C. for 10 min. After cooling to RT, the reaction was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customreacted in a microwave at 160° C. for 10 min
  2. customthe reaction was purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-0ed31037f15b4edbb7282241195a81c2
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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