Formamide → HCID 135928897, compound

HRID 1685100Notes

Reaction equation

HRID 1685100 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[CH:10]3)=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:4][C:3]=1[C:22]([O:24]C)=O.C([O-])=O.[NH4+].[CH:30]([NH2:32])=O>>[NH:12]1[C:13]2[C:9](=[CH:8][C:7]([C:6]3[C:2]4[N:1]=[CH:30][NH:32][C:22](=[O:24])[C:3]=4[S:4][C:5]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:15][CH:14]=2)[CH:10]=[CH:11]1

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 67265010HCID 67265010, compound

Product 1

HCID 135928897HCID 135928897, compound

Procedure

A mixture of EXAMPLE 8B (95 mg, 0.27 mmol) and ammonium formate (68 mg, 1.08 mmol) in formamide (5 mL) was heated at 170° C. for 4 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by reverse phase HPLC on a C18 column using 0-70% acetonitrile/0.1% trifluoroacetic acid in water to give 40 mg of the title compound. 1H NMR (DMSO-d6) δ 12.57 (br, 1H), 11.14 (s, 1H), 8.15 (s, 1H), 7.53 (s, 1H), 7.30-7.36 (m, 7H), 6.93 (dd, J=8.2, 1.5, 1H), 6.41 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase HPLC on a C18 column

Sources & evidence

ORD record
ord-cba96d4598294de5a427f3eade66a4d9
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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