Hydrochloric Acid → HCID 67275454, compound

HRID 1696949Notes

Reaction equation

HRID 1696949 reaction equation
[CH2:1]([NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]2[N:24]=[C:23]3[C:18]([C:19](=[O:39])[C:20]([C:36]([OH:38])=[O:37])=[CH:21][N:22]3CC3C=CC(OC)=CC=3OC)=[CH:17][C:16]=2[F:40])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.ClCCl.Cl>FC(F)(F)C(O)=O.C(OCC)C>[CH2:1]([NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]2[N:24]=[C:23]3[C:18]([C:19](=[O:39])[C:20]([C:36]([OH:38])=[O:37])=[CH:21][NH:22]3)=[CH:17][C:16]=2[F:40])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 67275522HCID 67275522, compound

Product 1

HCID 67275454HCID 67275454, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 244B (0.027 g) in trifluoroacetic acid (2 mL) was heated at 75° C. for 18 hours, and concentrated with a toluene azeotrope; and the residue was purified on a reverse phase HPLC on a C8 column with 10-95% acetonitrile in water containing 0.1% trifluoroacetic acid to provide an oily compound. A solution of the oily compound in 1:1 of methanol/dichloromethane was treated with 2N HCl in diethyl ether (0.5 mL), and concentrated. NMR (DMSO-d6) δ ppm 13.34 (m, 1H), 9.72 (bs, 2H), 8.51 (d, 1H), 8.05 (d, 1H), 7.63 (m, 2H), 7.44 (m, 3H), 4.74 (bs, 1H), 4.40-4.00 (m, 5H), 3.70 (m, 2H).

Workup

  1. concentrationconcentrated with a toluene azeotrope
  2. customand the residue was purified on a reverse phase HPLC on a C8 column with 10-95% acetonitrile in water containing 0.1% trifluoroacetic acid
  3. customto provide an oily compound
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38f1a5d98cb04f42b9537084d2282fd1
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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