Acetyl chloride → HCID 24995286, compound

HRID 1972165Notes

Reaction equation

Cl.Cl.[Br:3][C:4]1[C:5]([O:22][C:23]2[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=2[Cl:37])[C:26]([NH:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[O:27])=[CH:6][C:7]([NH:10][C:11]2[S:15][N:14]=[C:13]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:12]=2)=[N:8][CH:9]=1.CCN(C(C)C)C(C)C.[C:47](Cl)(=[O:49])[CH3:48]>CN(C=O)C>[C:47]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[N:12]=[C:11]([NH:10][C:7]3[CH:6]=[C:5]([O:22][C:23]4[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=4[Cl:37])[C:26]([NH:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[O:27])[C:4]([Br:3])=[CH:9][N:8]=3)[S:15][N:14]=2)[CH2:17][CH2:18]1)(=[O:49])[CH3:48]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(5-Bromo-2-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)pyridin-4-yloxy)-4-chloro-N-(2-(dimethylamino)ethyl)benzamide dihydrochloride (0.12 g, 0.18 mmol) was dissolved in DMF (2 mL) and the solution was cooled to 0° C. DIEA (0.13 mL, 0.73 mmol) was added followed by acetyl chloride (0.017 mL, 0.24 mmol). The solution was warmed to ambient temperature. After 15 minutes, the solution was quenched with water, extracted with EtOAc, dried, and concentrated. HPLC purification gave the title compound (0.0066 g, 6%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.69-1.76 (m, 1H), 1.81-1.88 (m, 1H), 1.86-2.12 (m, 2H), 2.04 (s, 3H), 2.26 (s, 6H) 2.60 (t, 2H), 2.78-2.85 (m, 1H), 2.95-3.04 (m, 1H), 3.13-3.21 (m, 1H), 3.54-3.60 (m, 2H), 3.78-3.84 (m, 1H), 4.41-4.46 (m, 1H), 6.15 (s, 1H), 7.40 (s, 1H), 7.53 (d, 1H), 7.59-7.64 (m, 3H), 8.49 (s, 1H).

Workup

temperatureThe solution was warmed to ambient temperature
customthe solution was quenched with water
extractionextracted with EtOAc
customdried
concentrationconcentrated
customHPLC purification

Sources & evidence

ORD record: ord-a8a2fe28cec34c719db5ed931dbeb748
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431713B2

Reaction notes

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