Trityl chloride → HCID 69124867, compound

HRID 2183189Notes

Reaction equation

HRID 2183189 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][NH:10][C:9]3([Br:23])[C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[O:16])=[N:2]1.[C:24]1([C:30](Cl)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>CN(C)C=O>[Br:23][C:9]1([C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[O:16])[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:3]3[N:4]=[CH:5][N:1]([C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:2]=3)[CH:7]=2)[NH:11][NH:10]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178519605HCID 178519605, compound

Product 1

HCID 69124867HCID 69124867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(5-(1H-1,2,4-triazol-3-yl)-3-bromo-1H-indazoyl)perhydro-2H-pyran in 60 mL in dimethyl formamide, was added triphenylmethyl chloride (3.48 g, 12.5 mmol), and triethyl amine (4.64 mL, 33.32 mmol). The reaction mixture was heated to 80° C. for 12 hours. The solvent was removed under reduced pressure and the crude reaction mixture was partitioned between water and ethyl acetate. The oil resulting from evaporation of the extracts was purified by column chromatography (SiO2, 25% ethyl acetate in hexanes (2.90 g, 61% over 4 steps): 1H NMR (CDCl3) δ 8.3 (s, 1H), 8.2 (d, 1H), 7.9 (s, 1H), 7.5 (d, 1H), 7.4-8.1 (m, 15H), 5.68 (dd, 1H), 4.0 (m, 1H), 3.75 (m, 1H), 2.5 (m, 1H), 2.1 (m, 2H), 1.7 (m, 3H); ES-MS (m/z) 592 [M+2]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. customThe oil resulting from evaporation of the extracts
  5. customwas purified by column chromatography (SiO2, 25% ethyl acetate in hexanes (2.90 g, 61% over 4 steps)

Sources & evidence

ORD record
ord-267861ffcd7c40589abef3f134f94990
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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