Acetyl chloride → HCID 24995286, compound

HRID 911098Notes

Reaction equation

HRID 911098 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

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 66618144HCID 66618144, compound

Product 1

HCID 24995286HCID 24995286, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 RT. After 15 minutes, the solution was quenched with water, extracted with EtOAc, dried, and concentrated. HPLC purification gave 3-(2-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-bromopyridin-4-yloxy)-4-chloro-N-(2-(dimethylamino)ethyl)benzamide (0.0066 g, 6%) as a white solid. 1H NMR (400 MHz, CDCl3) 01.69-1.76 (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

  1. temperatureThe solution was warmed to RT
  2. customthe solution was quenched with water
  3. extractionextracted with EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customHPLC purification

Sources & evidence

ORD record
ord-48674d3ad09947c895f71519ab2984e8
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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