1-Bromo-2-Chloroethane → HCID 59361833, compound

HRID 61676Notes

Reaction equation

[C:1]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29]([C:33]([O-:35])=[O:34])[N:28]=[CH:27]4)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:36])[CH:19]=3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:44][CH2:45][Cl:46]>CN(C=O)C>[C:1]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29]([C:33]([O:35][C:9]([CH3:13])([CH3:10])[CH3:8])=[O:34])[N:28]=[CH:27]4)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:36][CH2:44][CH2:45][Cl:46])[CH:19]=3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of 5-(2-(3-butyramidophenyl)-6-hydroxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate (1.50 g, 2.79 mmol) and potassium carbonate (1.64 g, 11.8 mmol) in anhydrous DMF (5 mL) was added 1-bromo-2-chloroethane (1.6 g, 11.2 mmol) The subsequent mixture was heated at 85° C. for 4 h, upon which it was allowed to cool to RT and it was poured onto ice-water. A solid was precipitated out, which collected via filtration and dried under vacuum. The solid was purified via silica gel column chromatography to give tert-butyl 5-(2-(3-butyramidophenyl)-6-(2-chloroethoxy)-quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.94 g, 1.56 mmol, 60%). HPLC retention time 7.479.

Workup

temperatureto cool to RT
additionit was poured onto ice-water
customA solid was precipitated out
filtrationwhich collected via filtration
customdried under vacuum
customThe solid was purified via silica gel column chromatography

Sources & evidence

ORD record: ord-0a2a882c9fd14ae38a9a89eb1f24c47c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440961B2

Reaction notes

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