2,4-Dichloroquinazoline → HCID 178478401, compound

HRID 2082019Notes

Reaction equation

HRID 2082019 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) δ9.30 (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-06427182d14c4c92a4d4defbd195c8cb
Source dataset
uspto-grants-1993_02
Patent number
US05187168

Reaction notes

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