Water → HCID 178491569, compound

HRID 1503847Notes

Reaction equation

HRID 1503847 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[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]([CH2:31][C:32](=[O:38])[N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:27][C:26]=2[O:39][CH3:40])[N:6]=1.O.C(=O)(O)[O-:48].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[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:48])=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32](=[O:38])[N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:27][C:26]=2[O:39][CH3:40])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86725396HCID 86725396, compound

Product 1

HCID 178491569HCID 178491569, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

The product of Example 30E (80 mg, 0.12 mmol) was dissolved in concentrated sulfuric acid (3 mL) and water (0.5 mL) was added and the solution was heated at 85° C. for 0.5 hours. After cooling to ambient temperature, the mixture was neutralized with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 14.11 (s, 1 H), 11.83 (s, 1 H), 9.59 (s, 1 H), 8.59 (s, 1 H), 7.71-7.68 (m, 2 H), 7.60-7.58 (m, 2 H), 7.44 (t, J=7.8 Hz, 1 H), 6.77 (s, 1 H), 6.31 (d, J=8.1 Hz, 1 H), 4.79 (s, 2 H), 3.81 (s, 3 H), 3.51 (s, 2 H), 3.46 (t, J=6.6 Hz, 2 H), 3.33 (t, J=6.3 Hz, 2 H), 1.93-1.78 (m, 4 H). MS: 553 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7e7174d2f00f4e16b81fd95f99162275
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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