Ammonia → Formate

HRID 535943Notes

Reaction equation

HRID 535943 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]=12)=[O:9])[C:4](Cl)=[O:5].[NH3:28].C1[CH2:33][O:32]CC1>CO>[NH2:28][C:4](=[O:5])[C@@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]=12)=[O:9])[C:2]([CH3:27])([CH3:26])[CH3:1].[CH:33]([O-:32])=[O:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 57635097HCID 57635097, compound

Product 2

HCID 283FormateYield 15%HCID 57635143HCID 57635143, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 23A (0.11 g, 0.3 mmol) was dissolved in THF (2 mL) and 7M ammonia solution in methanol was added. The resulting mixture was stirred for 2 h, the solvent was evaporated and the residue was purified by prep LC/MS using 5-95% gradient acetonitrile/water with 0.1% formic acid to give Compound 285 as a formate salt (20 mg, 15%). 1H-NMR (400 MHz, CD3OD) δ: 1.11 (s, 9H), 2.59 (s, 3H), 2.93 (m, 2H), 4.09 (m, 2H), 4.21 (m, 2H), 4.40 (m, 1H), 7.51 (m, 3H), 7.72 (m, 2H), 8.31 (s, 1H); LCMS (+ESI) m/z 370.2 [M+H]+.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by prep LC/MS

Sources & evidence

ORD record
ord-663e152d6beb45e1a753b3e5e8085221
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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