Stannous Chloride → HCID 67568849, compound

HRID 1418399Notes

Reaction equation

HRID 1418399 reaction equation
[ClH:1].[N:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[N:22]=[C:21]([NH2:23])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1)=[N+]=[N-].[Sn](Cl)[Cl:25]>CO>[ClH:25].[ClH:1].[NH2:2][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[N:22]=[C:21]([NH2:23])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 86753883HCID 86753883, compound

Product 1

HCID 67568849HCID 67568849, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(2-azidoethyl)phenyl)-1,2-dihydro-4-quinazolinamine hydrochloride (Example 50, 0.38 g, 1.16 mmol) in methanol (10 ml) was added tin dichloride (0.33 g, 1.73 mmol) and the mixture stirred for 2 h (effervescence). Evaporation and purification by RPHPLC eluting with trifluoroacetic acid/water/methanol (1:90:10, increasing the gradient to 1:5:95) gave the product, MS (+FAB) 266 ([M+H]+), 1H NMR (d6 -DMSO) 10.07 (1H, s), 9.29 (1H, s), 8.51 (1H, s), 7.98 (2H, s), 7.91 (1H, s), 7.69 (1H, d), 7.33-7.55 (4H, m), 6.7-7.0 (2H, m), 6.17 (1H, s), 2.9-3.1 (4H, m).

Workup

  1. customEvaporation and purification by RPHPLC
  2. washeluting with trifluoroacetic acid/water/methanol (1:90:10
  3. temperatureincreasing the gradient to 1:5:95)
  4. customgave the product, MS (+FAB) 266 ([M+H]+), 1H NMR (d6 -DMSO) 10.07 (1H, s), 9.29 (1H, s), 8.51 (1H, s), 7.98 (2H, s), 7.91 (1H, s), 7.69 (1H, d), 7.33-7.55 (4H, m), 6.7-7.0 (2H, m), 6.17 (1H, s), 2.9-3.1 (4H, m)

Sources & evidence

ORD record
ord-52f372eb6fd6440f8626da7d894dce31
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

Loading…