HCID 90411586, compound → HCID 90411860, compound

HRID 1754616Notes

Reaction equation

HRID 1754616 reaction equation
[C:1]([Si:5]([CH3:33])([CH3:32])[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:25]=[CH:24][C:23]([N:26]2C=NC=N2)=[N:22][C:21]1=[O:31])[C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:10])([CH3:4])([CH3:3])[CH3:2]>N.CO>[C:1]([Si:5]([CH3:32])([CH3:33])[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[N:22][C:21]1=[O:31])[C@H:9]([O:11][Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 90411586HCID 90411586, compound

Product 1

HCID 90411860HCID 90411860, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 43 (2.0 g, 4.05 mmol) in 60 ml of 6 M NH3/MeOH was heated at 100° C. in a Parr bomb for 2 days. The reaction was cooled, concentrated and chromatographed on silica eluting, first, with ethyl acetate and, second, with 5% MeOH in ethyl acetate. Concentration of the product-containing fractions afforded 1.2 g (67%) of 44 as a white solid. 1H NMR (DMSO-d6): δ 7.39 (d, J=7 Hz, 1H), 6.94 (br s, 2H), 5.60 (d, J=7 Hz, 1H), 4.00 (m, 1H), 3.65 (m, 1H), 3.53 (m, 3H), 2.02 (m, 1H), 1.13 (d, J=6 Hz, 3H), 0.86 (s, 9H), 0.84 (s, 9H), 0.04 (s, 6H), −0.01 (s, 3H), −0.02 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customchromatographed on silica eluting

Sources & evidence

ORD record
ord-2ac051ae7bde405fa6fb13ab4d251034
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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