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

HRID 1497612Notes

Reaction equation

HRID 1497612 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

Prepared according to Procedure A from 6-bromo-4-chloroquinazoline (5.0 g) and 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).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-935f8a60fee2416b81f044c9893df114
Source dataset
uspto-grants-2015_12
Patent number
US09199973B2

Reaction notes

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