Diisopropylethylamine → HCID 67354913, compound

HRID 522901Notes

Reaction equation

HRID 522901 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([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: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(CC)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]=[CH:6][N:5]=[C:4]([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:3]=3)[CH2:29]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochlorideHCID 86685253HCID 86685253, compound

Product 1

HCID 67354913HCID 67354913, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
84 °C

Procedure

To 3-(6-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 at RT was added 2-propanol (2 mL) followed by N,N-diisopropylethylamine (0.179 mL, 1.028 mmol). The resulting reaction mixture was heated to 84° C. for 51 h, cooled to RT, concentrated, purified using MPLC (5 g cartridge, 12 g column, 0 to 65% 90/10 CH2Cl2-MeOH in CH2Cl2) giving 3-(6-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-4-ylamino)-N-methylbenzamide (135.0 mg).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-691334cd999c4b97b3b9d1ad105ef145
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

Loading…