Tetrahydrofuran → HCID 50942992, compound

HRID 2038393Notes

Reaction equation

HRID 2038393 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[N:11]=[C:12]([C:24]([OH:26])=O)[S:13][C:14]=2[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C1CN([P+](ON2N=[N:51][C:46]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C([N:63](CC)C(C)C)(C)C.[O:69]1CC[CH2:71][CH2:70]1>ClCCl>[C:22]([C:17]1[CH:16]=[C:15]([C:14]2[S:13][C:12]([C:24]([N:63]3[CH2:71][C:70](=[O:69])[NH:51][CH2:46]3)=[O:26])=[N:11][C:10]=2[C:5]2[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:20]=[C:19]([F:21])[CH:18]=1)#[N:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70336257HCID 70336257, compound

Product 1

HCID 50942992HCID 50942992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

45.0 mg of the compound from Example 32A having a purity of 61% (0.075 mmol), 16.5 mg (0.082 mmol) of the compound from Example 20A and 58.3 mg (0.112 mmol) of PyBOP are provided in 3 ml of tetrahydrofuran, and 42 μl (0.239 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, acetonitrile is then added to the crude product and the solid formed is subsequently collected by filtration. 17.4 mg (53% 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, acetonitrile
  5. additionis then added to the crude product
  6. customthe solid formed
  7. filtrationis subsequently collected by filtration

Sources & evidence

ORD record
ord-220e9890962244cfaf095470ab836139
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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