Diisopropylethylamine → HCID 67353768, compound

HRID 522903Notes

Reaction equation

HRID 522903 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[CH:5]=[CH:4][N:3]=1.Cl.[F:20][C:21]1[CH:31]=[CH:30][C:24]([O:25][CH:26]2[CH2:29][NH:28][CH2:27]2)=[CH:23][CH:22]=1.C(N(C(C)C)C(C)C)C>CC(O)C>[F:20][C:21]1[CH:31]=[CH:30][C:24]([O:25][CH:26]2[CH2:27][N:28]([C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=4)[C:12]([NH:14][CH3:15])=[O:13])[CH:5]=[CH:4][N:3]=3)[CH2:29]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochlorideHCID 86685254HCID 86685254, compound

Product 1

HCID 67353768HCID 67353768, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
84 °C

Procedure

To 3-(2-chloropyrimidin-4-ylamino)-N-methylbenzamide (90.0 mg, 0.343 mmol) and 3-(4-fluorophenoxy)azetidine hydrochloride (73.3 mg, 0.360 mmol) in a disposable sealed tube in 2-propanol (2.00 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.179 mL, 1.028 mmol). The resulting reaction mixture was heated at 84° C. for 48 h, cooled to RT, filtered, rinsed with IPA, and concentrated under reduced pressure to afford 3-(2-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-ylamino)-N-methylbenzamide (102.3 mg).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. filtrationfiltered
  4. washrinsed with IPA
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4eba6a1c81004037a42e04c37e6652be
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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