Dichloromethane → HCID 178509262, compound

HRID 337827Notes

Reaction equation

HRID 337827 reaction equation
[Cl:1][C:2]1[C:3]([O:30][C@H:31]2[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]2[C:37]2[C:38]([N+:48]([O-])=O)=[N:39][N:40](C3CCCCO3)[CH:41]=2)=[CH:4][C:5]([F:29])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.ClCCl>CO>[NH2:48][C:38]1[C:37]([C@H:32]2[CH2:33][CH2:34][CH2:35][CH2:36][C@@H:31]2[O:30][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:9])=[O:10])=[C:5]([F:29])[CH:4]=2)=[CH:41][NH:40][N:39]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 89963040HCID 89963040, compound

Product 1

HCID 178509262HCID 178509262, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 22c by using the 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-({(1S*,2R*)-2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]cyclohexyl}oxy)-N-(pyrimidin-4-yl)benzenesulfonamide (264 mg, 0.362 mmol) prepared in Example 71a, triethylsilane (0.10 mL), trifluoroacetic acid (0.5 mL), dichloromethane (2.0 mL) and methanol (1.0 mL), to yield the title compound (162 mg, 90%) as a white solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-027696718af240c9b63e10851abe1a76
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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