Triethylamine → (1-Benzyl-1H-indazol-5-yl)-(6-bromoquinazolin-4-yl)amine

HRID 1936752Notes

Reaction equation

HRID 1936752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:18]=[CH:17]2.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C.O>[CH2:23]([N:19]1[C:20]2[C:16](=[CH:15][C:14]([NH:13][C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=4)[N:8]=[CH:7][N:6]=3)=[CH:22][CH:21]=2)[CH:17]=[N:18]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2120691-(Phenylmethyl)-1H-indazol-5-amineHCID 167703106-Bromo-4-chloro-quinazoline

Product 1

HCID 21951963(1-Benzyl-1H-indazol-5-yl)-(6-bromoquinazolin-4-yl)amineYield 83.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-4-chloroquinazoline (5.0 g) was reacted with 5-amino-1-benzyl-1H-indazole (5.0 g) in acetonitrile (100 ml) at 100° C. The resulting precipitate was treated with triethylamine in ethyl acetate and water to give the title compound as a yellow solid, (7.37 g); δH [2H6]-DMSO 9.93(1H,s), 8.82 (1H,d), 8.52(1H,s), 8.19(1H,s), 8.09(1H,s), 7.92(1H,dd), 7.65(3H,m), 7.25(5H,m), 5.62(2H, s),

Sources & evidence

ORD record
ord-2fb8650932b6498faf4919d22d2d757c
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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