Aminoacetaldehyde dimethyl acetal → HCID 178433646, compound

HRID 2271119Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:22](=[O:23])[C:11]3=[CH:12][NH:13][C:14]([CH3:21])=[C:15]([CH2:16][CH2:17][CH2:18][C:19]#[N:20])[C:10]3=[N:9]2)=[CH:4][CH:3]=1.CO[CH:26](OC)[CH2:27][NH2:28]>CS(C)=O.[Cu]Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:22](=[O:23])[C:11]3=[CH:12][NH:13][C:14]([CH3:21])=[C:15]([CH2:16][CH2:17][CH2:18][C:19]4[NH:28][CH:27]=[CH:26][N:20]=4)[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the product of Example 107 (0.131 g, 0.4 mmol) and aminoacetaldehyde dimethylacetal (43 μl, 0.4 mmol) in DMSO (1 ml) was added copper(I) chloride (0.04 g, 0.4 mmol) and the mixture heated at 100° C. for 120 hours. The solvent was removed in vacuo and the residue suspended in formic acid (10 ml) and heated at 70° C. for 18 hours. The reaction was filtered and the solvent evaporated from the filtrate in vacuo. The crude product was purified by flash chromatography (silica gel, 6-10% MeOH/CH2Cl2) to give the title compound as a yellow solid (0.012 g, 8.1%). 1H NMR (360 MHz, CD3OD) δ8.34 (1H, s), 8.02 (2H, d, J 8.7 Hz), 7.42 (2H, d, J8.7 Hz), 7.11 (2H, br s), 2.99 (2H, br s), 2.80 (2H, br s), 2.40 (3H, s), 2.05 (2H, br s); MS (ES+) m/z 368/370 [MH]+.

Workup

customThe solvent was removed in vacuo
temperatureheated at 70° C. for 18 hours
filtrationThe reaction was filtered
customthe solvent evaporated from the filtrate in vacuo
customThe crude product was purified by flash chromatography (silica gel, 6-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-f6d63676aca5444d9a7237642f9335b8
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333336B1

Reaction notes

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