1,2-Dichloroethane → [1-(3-Fluoro-benzyl)-1H-indazol-5-yl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride

HRID 415023Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[CH2:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=2)[CH:20]=[N:19]1.ClCCCl>CC(O)(C)C>[ClH:1].[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[CH2:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH:27][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:24][CH:25]=2)[CH:20]=[N:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

Follow general procedure from Example 1, step E. 4-chloro-6-iodoquinazoline (1.18 g, 4.06 mmol) is mixed with 1-(3-Fluoro-benzyl)-1H-indazol-5-ylamine (1.09 g, 4.52 mmol), and a mixture of DCE (10 ml) and t-BuOH (10 ml) is added. The mixture is heated at 90° C. (oil bath temperature) for 8 hours. At 5 hours of heating LC/MS reveals substantial amount of product. Yield is 1.35 g (56%).

Workup

additionis added

Sources & evidence

ORD record: ord-ac013447405c4ca0bfa56735ec193f04
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088766B2

Reaction notes

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