Sodium Formate → HCID 11545673, compound

HRID 1695298Notes

Reaction equation

HRID 1695298 reaction equation
[CH:1]([O-])=[O:2].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:28])[C:12]2[NH:18][C:17]3[C:19]([Cl:24])=[CH:20][C:21]([NH2:23])=[CH:22][C:16]=3[CH2:15][S:14](=[O:26])(=[O:25])[C:13]=2[CH:27]=1)=[O:8]>C(O)=O>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:28])[C:12]2[NH:18][C:17]3[C:19]([Cl:24])=[CH:20][C:21]([NH:23][CH:1]=[O:2])=[CH:22][C:16]=3[CH2:15][S:14](=[O:26])(=[O:25])[C:13]=2[CH:27]=1)=[O:8]

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 11523493HCID 11523493, compound

Product 1

HCID 11545673HCID 11545673, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Sodium formate (0.074 g, 0.108 mmol) was added to a suspension of compound of Example 37 (0.20 g, 0.547 mmol) in formic acid (2 mL) and refluxed for 1.5 h. The reaction mixture was cooled and poured into ice water (50 mL). The solid precipitated was filtered, washed with water and dried. The crude product was purified by trituration with chloroform/methanol (3:1) to obtain the title compound. Yield: 0.18 g (84%); mp: 280-282° C.; 1H NMR (DMSO-d6, 300 MHz): δ 2.48 (s, 3H, CH3), 3.82 (s, 3H, OCH3), 4.91 (s, 2H, CH2, trans minor isomer), 4.97 (s, 2H, CH2, cis major isomer), 7.30 (d, 1H, Ar, trans minor isomer), 7.47 (d, 1H, Ar, trans minor isomer), 7.56 (s, 1H, Ar, cis major isomer), 7.63 (s, 1H, Ar, cis major isomer), 7.89 (s, 1H, Ar), 7.94 (s, 1H, Ar), 8.26 (s, 1H, CHO, cis major isomer), 8.29 (s, 1H, NH), 8.78 (d, 1H, CHO, trans minor isomer), 10.40 (d, 1H, NH, trans minor isomer), 10.46 (s, 1H, NH, cis major isomer); MS: m/e (ES+) 395 (M+1); analysis: C17H14ClNO6S requires C, 51.72H, 3.83, N, 7.10, Cl, 8.98, S, 8.12; found C, 51.24,H, 3.80, N, 6.79, Cl, 9.22, S, 7.84%.

Workup

  1. temperaturerefluxed for 1.5 h
  2. temperatureThe reaction mixture was cooled
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified by trituration with chloroform/methanol (3:1)

Sources & evidence

ORD record
ord-14e38307af504943b6de17c709006c11
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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