3-Bromopropylamine hydrobromide → HCID 29799054, compound

HRID 920311Notes

Reaction equation

ClC1N=C(OC[C:10]2[CH:11]=[CH:12][C:13]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[C:14]([CH:17]=2)[C:15]#[N:16])C=C(Cl)N=1.CCN(C(C)C)C(C)C.Br.BrCCCN>CN(C)C=O>[F:26][C:25]([F:27])([F:28])[C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][C:13]1[CH:12]=[CH:11][CH:10]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(((2,6-dichloropyrimidin-4-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (600 mg, 1.363 mmol) and DIPEA (1.5 mL, 8.59 mmol) in N,N-dimethylformamide (3 ml) was added 3-bromopropan-1-amine hydrobromide (900 mg, 4.11 mmol) at 0° C. and the reaction mixture was stirred overnight at 0° C. The solution was purified with reverse phase column chromatography (120 g) using water (contained 0.3% TFA) and MeCN as eluent to afford 5-(((6-(3-bromopropyl)amino)-2-chloropyrimidin-4-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (350 mg, 0.646 mmol, 47.4% yield).

Workup

customThe solution was purified with reverse phase column chromatography (120 g)

Sources & evidence

ORD record: ord-dfafcf00ec9b4aab88624aa7da4d43d7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273054B2

Reaction notes

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