1-Hydroxybenzotriazole → HCID 118092837, compound

HRID 2207401Notes

Reaction equation

HRID 2207401 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C1C=CC2N(O)N=NC=2C=1.[CH3:18][C:19]1[CH:20]=[C:21]([C:36]2[CH:37]=[CH:38][C:39]([C:42](O)=[O:43])=[N:40][CH:41]=2)[CH:22]=[C:23]([NH:25][C:26]2[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=2)[CH:24]=1>CN(C=O)C>[CH3:18][C:19]1[CH:20]=[C:21]([C:36]2[CH:37]=[CH:38][C:39]([C:42]([N:4]3[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]3)=[O:43])=[N:40][CH:41]=2)[CH:22]=[C:23]([NH:25][C:26]2[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 231360Piperazin-2-oneHCID 118092560HCID 118092560, compound

Product 1

HCID 118092837HCID 118092837, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperazin-2-one (80.0 mg, 0.801 mmol), silica-bound carbodiimide (1.08 mmol/g load, 989 mg, 1.07 mmol), and HOBT (123 mg, 0.801 mmol) were added to a solution of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxylic acid (200 mg, 0.534 mmol) in DMF (5.30 mL) and the reaction mixture was stirred at room temperature overnight. Macroporous-carbonate (3.17 mmol/g load, 1.01 g, 3.21 mmol) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was filtered, washed with DMF and was concentrated under reduced pressure. The residue was triturated with dichloromethane and was isolated by filtration (cold ether wash) to yield 4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]carbonyl}piperazin-2-one. MS APCI calc'd for C22H20F3N6O2 [M+H]+ 457. found 457. 1H NMR (500 MHz, DMSO-d6) δ 10.30 (s, 1H), 8.84 (d, J=5.5 Hz, 2H), 8.14 (s, 2H), 8.00 (s, 1H), 7.76 (t, 1H), 7.60 (s, 1H), 7.32-7.13 (m, 2H), 4.16 (d, J=12.2 Hz, 2H), 3.92-3.77 (m, 1H), 3.72 (s, 1H), 2.37 (s, 3H).

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe reaction mixture was filtered
  3. washwashed with DMF
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was triturated with dichloromethane
  6. customwas isolated by filtration (cold ether wash)

Sources & evidence

ORD record
ord-fec92a3ed2674d9fb5441a2fc3b9735c
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…