Sodium Bicarbonate → HCID 178493691, compound

HRID 1503860Notes

Reaction equation

HRID 1503860 reaction equation
[Cl:1][C:2]1[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[C:3]=1[CH2:4][C:5]1[C:10]2[N:11]=[CH:12][N:13](COCC[Si](C)(C)C)[C:9]=2[C:8]([C:22]#[N:23])=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)=[C:27]([F:44])[C:26]=2[O:45][CH3:46])[N:6]=1.C(=O)(O)[O-:53].[Na+]>O.S(=O)(=O)(O)O>[Cl:51][C:47]1[CH:48]=[CH:49][CH:50]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[C:10]2[N:11]=[CH:12][NH:13][C:9]=2[C:8]([C:22]([NH2:23])=[O:53])=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]3)=[C:27]([F:44])[C:26]=2[O:45][CH3:46])[N:6]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86725403HCID 86725403, compound

Product 1

HCID 178493691HCID 178493691, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product of Example 43B (50 mg, 0.068 mmol) and 4 drops of water in sulfuric acid (1 mL) was heated at 90° C. for 40 minutes. The mixture was poured onto ice water, neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to provide the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 8.37 (s, 1H), 7.63(dd, J=2.1 Hz, J=9.3 Hz, 1H), 7.56 (s, 1H), 7.53 (s, 1H), 7.41 (m, 1H), 6.32 (t, J=9 Hz, 1H), 4.81 (s, 2H), 3.94 (s, 3H), 3.40 (m, 4H), 3.26 (m, 4H). MS: 544 (M+H+).

Workup

  1. additionThe mixture was poured onto ice water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cde07b8383824e4cb7642684a6c8a9a6
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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