Hydrochloric Acid → HCID 53482225, compound

HRID 1400858Notes

Reaction equation

HRID 1400858 reaction equation
[F:1][C:2]1[CH:37]=[C:36]([NH:38][C:39]([NH:41][C:42](=[O:51])[CH2:43][C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)=[S:40])[CH:35]=[CH:34][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]([CH2:30][CH2:31][O:32][CH3:33])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.Cl>C(O)(=O)C>[F:1][C:2]1[CH:37]=[C:36]([NH:38][C:39]([NH:41][C:42](=[O:51])[CH2:43][C:44]2[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=2)=[S:40])[CH:35]=[CH:34][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][CH2:30][CH2:31][O:32][CH3:33])=[CH:18][N:19]=3)[S:13][C:6]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86658593HCID 86658593, compound

Product 1

HCID 53482225HCID 53482225, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 186 (0.19 g, 0.26 mmol) in acetic acid (10 mL) was added aqueous HCl (3M, 1.0 mL, 3.0 mmol). The mixture was stirred at room temperature for 3 h then partially concentrated. The residue was partitioned between ethyl acetate and water, the organic phase was collected, washed with saturated aqueous sodium bicarbonate and brine. It was then dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (eluent 15% methanol/chloroform) to give title compound 187 (80 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.53 (d, J=5.5, 1H), 8.50 (d, J=1.6, 1H), 8.30 (s, 1H), 8.18 (d, J=7.8, 1H), 8.04 (dd, J=11.2, 1.6, 1H), 7.89 (dd, J=8.2, 2.2, 1H), 7.54-7.50 (m, 2H), 7.40-7.35 (m, 2H), 7.22-7.15 (m, 2H), 6.67 (d, J=5.5, 1H), 3.83 (s, 2H), 3.40 (s, 2H), 3.37 (t, J=5.7, 2H), 3.22 (s, 3H), 2.82-2.75 (m, 4H), 2.69 (t, J=5.7, 2H). LRMS (M+H): 634.4

Workup

  1. concentrationthen partially concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic phase was collected
  4. washwashed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialIt was then dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (eluent 15% methanol/chloroform)

Sources & evidence

ORD record
ord-484a970e24dc4c4493d5b4c3c5e343a8
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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