Piperidine → HCID 72944222, compound

HRID 1505699Notes

Reaction equation

HRID 1505699 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:13]3[N:18]=[CH:17][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH2:24][C:25](O)=[O:26])[CH:23]=4)=[CH:15][N:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:4]=[N:3]1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[CH:15][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH2:24][C:25]([N:28]5[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:26])[CH:23]=4)=[CH:17][N:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89924098HCID 89924098, compound

Product 1

HCID 72944222HCID 72944222, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (4-{2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]pyrimidin-5-yl}-1H-pyrazol-1-yl)acetic acid (example 9, 110 mg; 0.31 mmol; 1.0 eq.), piperidine (52 mg; 0.61 mmol; 2.0 eq.), HATU (174 mg; 0.46 mmol; 1.50 eq.) and DIEA (152 μl; 0.92 mmol; 3.0 eq.) in DMF (2 mL) was stirred at 50° C. O/N. The reaction mixture was poured into water and extracted with DCM (three times). Combined organic phases were then concentrated under reduced pressure and the residue was recrystallised in MeOH/Ether. The solid obtained was filtered and dried under reduced pressure to give the title compound as a white solid (20 mg, 15%). 1H NMR (300 MHz, DMSO) δ 9.18 (s, 2H), 8.54 (t, J=1.6 Hz, 1H), 8.37 (s, 1H), 8.27 (s, 1H), 8.25-8.19 (m, 1H), 8.14 (s, 1H), 7.93 (s, 1H), 7.77-7.66 (m, 1H), 7.52 (t, J=7.8 Hz, 1H), 5.22 (s, 2H), 3.90 (s, 3H), 3.55-3.39 (m, 4H), 1.69-1.39 (m, 6H).HPLC (Condition A): Rt 3.16 min (purity 99.9%). MS (ESI+): 428.3

Workup

  1. extractionextracted with DCM (three times)
  2. concentrationCombined organic phases were then concentrated under reduced pressure
  3. customthe residue was recrystallised in MeOH/Ether
  4. customThe solid obtained
  5. filtrationwas filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-040b655292fc4b16b46a09adb55b387f
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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