1-(4-Azidobenzoyl)-3-(pyrrolidin-1-ylmethyl)piperidine → 3-[1-(4-{[3-(pyrrolidin-1-ylmethyl)piperidin-1-yl]carbonyl}phenyl)-1H-1,2,3-triazol-4-yl]-1H-indazole

HRID 1520048Notes

Reaction equation

HRID 1520048 reaction equation
[N:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][N:27]=1)#[CH:25]>C(Cl)Cl>[N:17]1([CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][N:10]([C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:1]4[CH:25]=[C:24]([C:26]5[C:34]6[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=6)[NH:28][N:27]=5)[N:3]=[N:2]4)=[CH:23][CH:22]=3)=[O:9])[CH2:11]2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 866990111-(4-Azidobenzoyl)-3-(pyrrolidin-1-ylmethyl)piperidineHCID 178437996HCID 178437996, compound

Product 1

HCID 574067243-[1-(4-{[3-(pyrrolidin-1-ylmethyl)piperidin-1-yl]carbonyl}phenyl)-1H-1,2,3-triazol-4-yl]-1H-indazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following procedure described for intermediate 10, but starting from 1-(4-azidobenzoyl)-3-(pyrrolidin-1-ylmethyl)piperidine (420 mg; 1.34 mmol; 1.0 eq.) and 3-ethynyl-1H-indazole (190 mg; 1.34 mmol; 1.0 eq.). After purification by preparative HPLC, it was obtained as the formic acid salt. The salt was solubilized in DCM and washed with a saturated solution of NaHCO3 then brine. Organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting oil was suspended in EtOH, and concentrated to dryness to afford the title compound as a yellow powder. 1H NMR (300 Mz, DMSO-d6) δ: 13.37 (s, 1H), 9.37 (s, 1H), 8.36 (d, J=8.1 Hz, 1H), 8.15 (d, J=8.7 Hz, 2H), 7.61 (m, 3H), 7.43 (m, 1H), 7.26 (m, 1H), 4.48 (m, 0.4H), 4.25 (m, 0.6H), 3.70 (m, 0.6H), 3.52 (m, 0.4H), 3.04 (m, 0.4H), 2.91 (m, 0.6H), 2.74 (m, 0.4H), 2.20-2.43 (m, 4H), 2.02 (m, 0.6H), 1.69 (m, 6H), 1.48 (m, 4H), 1.20 (m, 1H). HPLC (Condition A): Rt 2.69 min (purity 99.9%). MS (ESI+): 456.4, MS (ESI−): 454.5.

Workup

  1. customThe title compound was prepared following procedure
  2. customAfter purification by preparative HPLC
  3. customit was obtained as the formic acid salt
  4. washwashed with a saturated solution of NaHCO3
  5. dry with materialOrganic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0f82e6851f5f493a87b67f59702c89c1
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

Loading…