Tetrahydrofuran → HCID 50943067, compound

HRID 2038394Notes

Reaction equation

HRID 2038394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:22]([OH:24])=O)[S:11][C:12]=2[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([C:20]#[N:21])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.C1CN([P+](ON2N=[N:49][C:44]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C([N:61](CC)C(C)C)(C)C.[O:67]1CC[CH2:69][CH2:68]1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:22]([N:61]3[CH2:69][C:68](=[O:67])[NH:49][CH2:44]3)=[O:24])[S:11][C:12]=2[C:13]2[CH:14]=[C:15]([C:20]#[N:21])[CH:16]=[C:17]([F:19])[CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70341698HCID 70341698, compound

Product 1

HCID 50943067HCID 50943067, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90.0 mg of the compound from Example 40A having a purity of 90% (0.226 mmol), 49.7 mg (0.248 mmol) of the compound from Example 20A and 176 mg (0.339 mmol) of PyBOP are provided in 5.0 ml of tetrahydrofuran, and 126 μl (0.722 mmol) of N,N-diisopropylethylamine are added at room temperature. The reaction solution is stirred at room temperature overnight, diluted with dichloromethane and subsequently washed with a 1N aqueous hydrogen chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure, and the crude product is then purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 62.0 mg (64% of theory) of the title compound are obtained.

Workup

  1. washsubsequently washed with a 1N aqueous hydrogen chloride solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude product is then purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-ee392ac580cb4592bb1abd065e3db16c
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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