Acetonitrile → HCID 178492025, compound

HRID 2174941Notes

Reaction equation

HRID 2174941 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1.[CH:22]([N:25]([CH:28](C)C)CC)(C)C.C(#[N:33])C>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:22](=[N:25][C:28]#[N:33])[N:13]([C:14]4[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 68285181HCID 68285181, compound2×

Product 1

HCID 178492025HCID 178492025, compound

Procedure

Diphenyl cyano carbonimidate (3.48 mmol) was added to a solution of 6-bromo-N4-(6-methoxypyridin-3-yl)quinoline-3,4-diamine (compound of step 3, 2.90 mmol) in dry acetonitrile (10 ml), followed by the addition of di-isopropyl ethyl amine (4.35 mmol). The resulting reaction mixture was refluxed for 48 h. The reaction mixture was cooled to RT, concentrated under vacuum and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 13.81 (s, 1H), 8.96 (s, 1H), 8.53 (d, J=3 Hz, 1H), 8.10 (d, J=3 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.80 (dd, J=9 Hz, 3 Hz, 1H), 7.20 (d, J=9 Hz, 1H), 7.13 (d, J=3 Hz, 1H), 4.00 (s, 3H); MS (m/z): 395 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 48 h
  3. concentrationconcentrated under vacuum
  4. custompurified (silica gel column, MeOH/CHCl3 as eluent)

Sources & evidence

ORD record
ord-cd2a19f9f7a0412b81d07720acdb3060
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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