Acetyl chloride → HCID 68061040, compound

HRID 1520071Notes

Reaction equation

HRID 1520071 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][CH:25]=[C:26]([CH:29]6[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]6)[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:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:35]([N:32]1[CH2:33][CH2:34][CH:29]([C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[C:20]3[C:18]2[N:17]=[N:16][N:15]([C:12]3[CH:13]=[CH:14][C:9]([C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:8])=[CH:10][CH:11]=3)[CH:19]=2)[CH2:30][CH2:31]1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 57406914HCID 57406914, compound

Product 1

HCID 68061040HCID 68061040, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-5-piperidin-4-yl-1H-indazole (100 mg; 0.22 mmol; 1.0 eq.) in Pyridine (1.5 mL) was added acetyl chlorid (15 μl; 0.22 mmol; 1.0 eq.). The reaction mixture was stirred at room temperature O/N. Acetyl chlorid (15 μl; 0.22 mmol; 1.0 eq.) was added again to the reaction mixture to complete the reaction. Pyridine was removed under reduced pressure and DCM was added to the residue. DCM phase was washed with a saturated solution of NH4Cl and brine, dried over magnesium sulfate, flittered and concentrated. The crude was purified by preparative chromatography to give the title compound as a white foam. 1H NMR (300 MHz, DMSO-d6) δ 13.30 (brs, 1H), 9.37 (s, 1H), 8.23-8.07 (m, 3H), 7.74-7.64 (m, 2H), 7.55 (d, J=8.6 Hz, 1H), 7.37 (dd, J=8.7 Hz, 1.4, 1H), 4.66-4.50 (m, 1H), 3.97 (d, J=13.2 Hz, 1H), 3.79-3.34 (m, 8H), 3.25-3.09 (m, 1H), 3.03-2.86 (m, 1H), 2.72-2.55 (m, 1H), 2.06 (s, 3H), 1.96-1.44 (m, 4H). HPLC (Condition A): Rt 3.09 min (purity 94.3%). MS (ESI+): 500.3, MS (ESI−): 498.3.

Workup

  1. customthe reaction
  2. customPyridine was removed under reduced pressure and DCM
  3. additionwas added to the residue
  4. washDCM phase was washed with a saturated solution of NH4Cl and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude was purified by preparative chromatography

Sources & evidence

ORD record
ord-ae2ea2c4dda143838bdfeb0432baba73
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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