Hydrochloric Acid → HCID 46927577, compound

HRID 882717Notes

Reaction equation

HRID 882717 reaction equation
[O:1]=[S:2]1(=[O:23])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17](O)=[O:18])[CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH2:4][NH:3]1.F[B-](F)(F)F.[N:29]1(OC(N(C)C)=[N+](C)C)[C:33]2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN.C1COCC1.Cl>ClCCl>[O:1]=[S:2]1(=[O:23])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([NH:29][CH3:33])=[O:18])[CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH2:4][NH:3]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67232902HCID 67232902, compound

Product 1

HCID 46927577HCID 46927577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid of Example 11 (0.66 mmol) is stirred overnight at ambient temperature in 50 ml of dichloromethane in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (0.80 mmol), diisopropylethylamine (0.80 mmol) and 2M methylamine solution in THF (1.32 mmol). The reaction mixture is then neutralised with 1N HCl solution, extracted with ethyl acetate, washed (saturated NaCl solution), dried (MgSO4), filtered and then evaporated under reduced pressure to yield, after triturating the residue in a dichloromethane/methanol mixture and filtering, the title product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed (saturated NaCl solution)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto yield
  7. customafter triturating the residue in a dichloromethane/methanol mixture
  8. filtrationfiltering

Sources & evidence

ORD record
ord-6330e070d5cc452c834611789bf808dc
Source dataset
uspto-grants-2012_08
Patent number
US08236790B2

Reaction notes

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