N-methyl-2-pyrrolidone → HCID 118308340, compound

HRID 1750575Notes

Reaction equation

HRID 1750575 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]1[N:21]=[CH:20][CH:19]=[N:18]1.CN1C(=O)CCC1.CCN(C(C)C)C(C)C.Br[C:40]1[N:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][N:41]=1>O>[CH3:16][C:14]1[CH:13]=[CH:12][C:11]([N:17]2[N:18]=[CH:19][CH:20]=[N:21]2)=[C:10]([CH:15]=1)[C:9]([NH:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[NH:2][C:40]1[N:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][N:41]=1)=[O:22]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 202926292-Bromo-5-(trifluoromethyl)pyrimidineHCID 118308085HCID 118308085, compound2×

Product 1

HCID 118308340HCID 118308340, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 100 mg, 0.31 mmol) and NMP (1 ml) was added DIPEA (0.200 mg, 1.56 mmol) and 2-bromo-5-(trifluoromethyl)pyrimidine (70 mg, 0.31 mmol). The mixture was subjected to microwave irradiation at 150° C. for 1 hour. Upon cooling, the reaction mass was poured into water (5 ml) and extracted with ethyl acetate (2×10 ml). The combined organics were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

  1. customirradiation at 150° C. for 1 hour
  2. temperatureUpon cooling
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record
ord-ee2da51bb2c84da5a5e9a2f9378e0b02
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…