HCID 57405010, compound → HCID 68060923, compound

HRID 1520084Notes

Reaction equation

HRID 1520084 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([C:20]4[C:28]5[C:23](=[CH:24][C:25]([C:29]#[C:30][CH2:31][OH:32])=[CH:26][CH:27]=5)[NH:22][N:21]=4)[N:17]=[N:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(Cl)Cl.CO.[Pd]>[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([C:20]4[C:28]5[C:23](=[CH:24][C:25]([CH2:29][CH2:30][CH2:31][OH:32])=[CH:26][CH:27]=5)[NH:22][N:21]=4)[N:17]=[N:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 57405010HCID 57405010, compound

Product 1

HCID 68060923HCID 68060923, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-6-yl)prop-2-yn-1-ol (40 mg; 0.09 mmol; 1.0 eq.) in DCM (2.0 mL) and MeOH (2.0 mL) was passed through a Pd/C cartridge at RT with full H2 at 1 mL/min in the H-cube. Solvents were removed under reduced pressure and the crude obtained was purified by preparative HPLC to give the title compound as a white solid (15 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ 13.23 (brs, 1H), 9.37 (s, 1H), 8.24 (d, J=8.3 Hz, 1H), 8.15 (d, J=8.6 Hz, 2H), 7.68 (d, J=8.6 Hz, 2H), 7.37 (m, 1H), 7.12 (dd, J=8.3 Hz, 1.1 Hz, 1H), 4.52 (t, J=5.1 Hz, 1H), 3.64 (m, 6H), 3.42 (m, 2H), 2.94-2.75 (m, 4H), 1.85-1.72 (m, 2H). HPLC (max plot) 98.3%; Rt % 2.69 min. UPLC/MS: (MS+) 433.1, (MS−) 431.2.

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe crude obtained
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-48c60ed37a8e4884aaf8a7b808d98dd1
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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