Morpholine → 2-[(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)methyl]-6-pyridin-4-ylpyridazin-3(2H)-one

HRID 1520069Notes

Reaction equation

[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[C:18]2[N:19]=[N:20][N:21]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=3)[CH:22]=2)[N:6]=[C:5]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH:4]=[CH:3]1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>>[N:38]1([C:27]([C:26]2[CH:30]=[CH:31][C:23]([N:21]3[CH:22]=[C:18]([C:12]4[C:11]5[C:15](=[CH:16][CH:17]=[C:9]([CH2:8][N:7]6[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:32]7[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=7)=[N:6]6)[CH:10]=5)[NH:14][N:13]=4)[N:19]=[N:20]3)=[CH:24][CH:25]=2)=[O:29])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 67981130HCID 67981130, compound

Product 1

HCID 574071112-[(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)methyl]-6-pyridin-4-ylpyridazin-3(2H)-one

Procedure

The title compound was obtained following procedure described for example 94, step b), but starting from 4-(4-{5-[(6-oxo-3-pyridin-4-ylpyridazin-1(6H)-yl)methyl]-1H-indazol-3-yl}-1H-1,2,3-triazol-1-yl)benzoic acid (65 mg; 0.12 mmol; 1.0 eq.) and morpholine (4 mL; 46 mmol; 372 eq.) to give the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 13.42 (s, 1H), 9.38 (s, 1H), 8.70 (dd, J=1.6, 4.6 Hz, 2H), 8.50 (s, 1H), 8.16 (d, J=6.0 Hz, 1H), 8.14 (d, J=3.0 Hz, 1H), 7.92 (dd, J=1.6, 4.6 Hz, 2H), 7.69 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.7 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H), 7.17 (d, J=9.8 Hz, 1H), 5.53 (s, 2H), 3.64 (s, 8H). HPLC (Condition A): Rt 2.24 min (purity 98.8%). MS (ESI+): 560.3, MS (ESI−): 558.2.

Sources & evidence

ORD record: ord-aa837d50a2a740c7a5b979b7c8abb9b3
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073892B2

Reaction notes

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