HCID 67813078, compound → HCID 67814679, compound

HRID 923645Notes

Reaction equation

HRID 923645 reaction equation
[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH2:3][N:4]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5]1.C(Cl)(=O)O.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:9]=[C:8]1[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5][N:4]1[CH2:3][C:2]([N:14]1[CH2:19][CH2:18][N:17]([C:25]([O:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:26])[CH2:16][CH2:15]1)=[O:1]

Participants

5

Reactant 2

HCID 67813078HCID 67813078, compoundHCID 86696914HCID 86696914, compound

Product 1

HCID 67814679HCID 67814679, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 10 (81.5 mg, 0.29 mmol) was treated with 4-nitrophenyl chloroformate carbonochloridate (213 mg, 1.06 mmol) and DMAP (108 mg, 0.88 mmol) in anhydrous CH2Cl2 (4 mL) at room temperature for 16 h. The mixture was washed successively with saturated NaHCO3(aq.) and 1 M HCl(aq) until the solution became transparent. The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of CH2Cl2/MeOH (100:0.5 to 9:1) to give the title compound (70 mg, 56% yield). C20H18N4O6S; pale yellow solid; mp 114-118° C.; IR vmax (neat) 2923, 2854, 1725, 1655, 1520, 1346, 1259, 1163, 1111, 1056, 1024, 862, 748 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.22 (2H, d, J=10.2 Hz), 8.02 (1H, d, J=8.0 Hz), 7.62 (2H, t, J=8.0 Hz), 7.55 (1H, d, J=8.0 Hz), 7.40 (1H, t, J=8.0 Hz), 7.27 (1H, d, J=10.2 Hz), 4.73 (2H, s), 3.70 (6H, br s), 3.62 (2H, br s); 13C NMR (100 MHz, CDCl3) δ 165.4, 165.1, 155.5, 151.7, 144.7, 141.0, 132.1, 126.5, 125.4, 124.9 (2×), 123.0, 122.0 (2×), 120.2, 44.7, 44.5, 44.2, 43.8, 43.6; ESI-HRMS calcd for C20H19N4O6S: 443.1025. found: m/z 443.1042 [M+H]+.

Workup

  1. washThe mixture was washed successively with saturated NaHCO3(aq.) and 1 M HCl(aq) until the solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column with elution of CH2Cl2/MeOH (100:0.5 to 9:1)

Sources & evidence

ORD record
ord-a91b82a35f964efe9548c5db02278212
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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