2,4-Dichloroquinazoline → HCID 178478401, compound

HRID 1657175Notes

Reaction equation

HRID 1657175 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH:14]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][CH:26]=2)=[N:17][N:16]=[N:15]1.C([O-])(=O)C.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18]3[NH:17][N:16]=[N:15][N:14]=3)=[CH:26][CH:27]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2528862,4-DichloroquinazolineHCID 517045Sodium AcetateHCID 178479176(4-(2-(1H-1,2,3,4-tetrazol-5-yl)phenyl)phenyl)methanamine hydrochloride

Product 1

HCID 178478401HCID 178478401, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 50 mL of tetrahydrofuran were added 2,4-dichloroquinazoline (0.30 g). N-[[-2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl amine hydrochloride (0.434 g) and 2.0 g of sodium acetate. The resulting suspension was stirred at room temperature for 53 hours at which time all the THF was removed by evaporation. The residue was purified by silica gel chromatography to yield 0.234 g of the desired product. (38%). The product was characterized as its sodium salt: 1H NMR (DMSO-d6, 400 MHz) δ 9.30 (t, J=5.9 Hz, 1H), 8.31 (d, J=7.8 Hz, 1H), 7.79 (m, 1H), 7.61 (d, J=8.4 Hz, 1H), 7.52 (m, 2H), 7.32 (m, 3H), 7.18 (d, J=8.2 Hz, 2H), 7.07 (d, J=8.2 Hz, 2H), 4.72 (d, J=5.8 Hz, 2H); negative FAB MS m/e 412 (M-Na)

Workup

  1. customwas removed by evaporation
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-64ef2d2b16724905862fa0925b79e267
Source dataset
uspto-grants-1993_10
Patent number
US05256781

Reaction notes

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