Hydrochloric Acid → HCID 16064795, compound

HRID 1991132Notes

Reaction equation

HRID 1991132 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[CH:17][N:16](OCC[Si](C)(C)C)[C:13]3=[N:14][CH:15]=2)[CH:4]=1.Cl>CCO>[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][C:10]2[CH:11]=[C:12]3[C:18]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68607641HCID 68607641, compound

Product 1

HCID 16064795HCID 16064795, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 68 (78 mg, 0.163 mmol), 10% aq. HCl (1.0 mL), EtOH (1.0 mL) was heated at 90° C. for 14 h. Purification by PTLC using AcOEt as eluent gave 69 as a white solid (22.8 mg, 40%); 1H NMR (400 MHz, CDCl3) δ 2.70 (s, 6H), 3.79 (s, 3H), 7.26 (m, 1H), 6.34 (ddd, J=8.3, 2.5, 0.7 Hz, 1H), 6.44 (t, J=2.1 Hz, 1H), 6.91 (t, J=8.0 Hz, 1H), 7.26 (s, 1H), 7.45 (s, 1H), 7.55 (d, J=0.7 Hz, 1H), 8.10 (d, J=2.0 Hz, 1H), 8.28 (d, J=1.9 Hz, 1H).

Workup

  1. customPurification by PTLC

Sources & evidence

ORD record
ord-6272b83aa7b3419484c839c551abcc85
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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