Toluene → HCID 21463011, compound

HRID 1940546Notes

Reaction equation

HRID 1940546 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[N:13][C:8]=2[NH:7][CH:6]=1)[CH3:3].[O:14]1[C:19]2=[CH:20][CH:21]=[C:22](N3CC=CCC3)[C:18]2=[CH:17][CH:16]=[CH:15]1.[C:29]1(C)[CH:34]=CC=C[CH:30]=1>>[O:14]1[C:15]2[CH:16]=[CH:17][C:18]([CH:3]3[CH2:34][CH:29]=[CH:30][CH2:1][N:2]3[CH2:4][C:5]3[C:9]4[C:8](=[N:13][CH:12]=[CH:11][CH:10]=4)[NH:7][CH:6]=3)=[CH:22][C:21]=2[CH:20]=[CH:19]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 70346440HCID 70346440, compound

Product 1

HCID 21463011HCID 21463011, compound

Conditions

Temperature
110 °C

Procedure

A suspension of 7-azagramine (180 mg, 1.0 mmol) and 4-benzofuran-5-yl-1,2,3,6-tetrahydropyridine (200 mg, 1.0 mmol) in toluene (5 ml) was heated at 110° C. for 16 h. The resulting hot solution was filtered and allowed to cool. The title compound (180 mg) crystallised and was collected by filtration as a white, crystalline solid, m.p. 168°-70° C.; (Found: C, 75.02; H, 5.81; N, 12.28. C21 H19N3O.0.33.H2O requires C, 75.20; H, 5.91; N, 12.53); δH (DMSO-d6) 2.50 (2H, br s, tetrahydropyridinyl CH2, obscured by solvent), 2.69 (2H, br s, CH2), 3.11 (2H, br s, tetrahydropyridinyl CH2), 3.76 (2H, s, ArCH2N), 6.12 (1H, br s, CH=CR), 6.91 (1H, s, ArH), 7.03 (1H, m, ArH), 7.40 (2H, m, ArH), 7.51 (1H, m, ArH), 7.64 (1H, s, ArH), 7.95 (1H, m, ArH), 8.04 (1H, m, ArH), 8.20 (1H, m, ArH), and 11.47 (1H, br s, NH); m/z (CI+, NH3) 330 (M+H)+.

Workup

  1. filtrationThe resulting hot solution was filtered
  2. temperatureto cool
  3. customThe title compound (180 mg) crystallised
  4. filtrationwas collected by filtration as a white, crystalline solid, m.p. 168°-70° C.

Sources & evidence

ORD record
ord-36b5f1d53918435a99e70362d5e0c19e
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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