Water → HCID 71075523, compound

HRID 595149Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:19][C:26](=[O:28])[CH3:27])[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Bromo-N-[4-(trifluoromethyl)pyrimidin-2-yl]benzene-1,3-diamine (1.06 g, 3.19 mmol) was dissolved in dichloromethane (15.9 ml) and pyridine (0.28 ml, 3.51 mmol) was added. The solution was cooled to 0° C. and then, acetyl chloride (0.23 ml, 3.19 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 1 hour. Water and dichloromethane were added and the organic phase was separated, dried and concentrated under reduced pressure to afford N-(3-bromo-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide as a beige powder. 1H NMR (400 MHz, Acetone-d6) δ 9.37 (s, 1H), 9.32 (s, 1H), 8.83 (d, J=6 Hz, 1H), 7.97 (s, 1H), 7.95 (s, 1H), 7.74 (s, 1H), 7.27 (d, J=6 Hz, 1H), 2.10 (s, 3H).

Workup

customthe organic phase was separated
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4a19c0bed849463eb0809d98f41fedbc
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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