Morpholine → 3-[1-(6-morpholin-4-ylpyridin-3-yl)-1H-1,2,3-triazol-4-yl]-1H-indazole

HRID 1520055Notes

Reaction equation

HRID 1520055 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][N:14]=3)[N:10]=[N:9]2)=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[N:22]1([C:2]2[N:7]=[CH:6][C:5]([N:8]3[CH:12]=[C:11]([C:13]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][N:14]=4)[N:10]=[N:9]3)=[CH:4][CH:3]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 772306093-[1-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-4-yl]-1H-indazole

Product 1

HCID 680609453-[1-(6-morpholin-4-ylpyridin-3-yl)-1H-1,2,3-triazol-4-yl]-1H-indazole

Conditions

Temperature
120 °C

Procedure

A suspension of 3-[1-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-4-yl]-1H-indazole (13 mg; 0.04 mmol; 1.0 eq.) in morpholine (0.5 mL) was heated in MW at 120° C. for 4.5 h. The precipitate obtained was filtered, washed with Et2O and dried under vacuum at 50° C. to afford the title compound as a beige solid. 1H NMR (DMSO-d6) δ: 13.33 (s, 1H), 9.18 (s, 1H), 8.74 (d, J=2.8 Hz, 1H), 8.34 (d, J=8.0 Hz, 1H), 8.16 (dd, J=2.6, 9.1 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.43 (m, 1H), 7.23 (m, 1H), 7.07 (d, J=9.1 Hz, 1H), 3.72 (m, 4H), 3.55 (m, 4H). HPLC (Condition A): Rt 3.21 min (purity 97.3%). MS (ESI+): 348.3, MS (ESI−): 346.3.

Workup

  1. customThe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with Et2O
  4. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-558074a8c2b64ecbb6f768a86f1c9d5e
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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