Sulfuric Acid → HCID 86713166, compound

HRID 1500277Notes

Reaction equation

HRID 1500277 reaction equation
[Cl:1][CH:2]([Cl:26])[C:3]([NH:5][C@H:6]([CH2:24][F:25])[C@@H:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([CH2:21][C:22]#[N:23])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[OH:8])=[O:4].S(=O)(=O)(O)[OH:28].C(=O)(O)[O-].[Na+]>>[NH2:23][C:22](=[O:28])[CH2:21][C:18]1[N:17]=[CH:16][C:15]([C:12]2[CH:11]=[CH:10][C:9]([C@@H:7]([OH:8])[C@H:6]([NH:5][C:3](=[O:4])[CH:2]([Cl:1])[Cl:26])[CH2:24][F:25])=[CH:14][CH:13]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86713167HCID 86713167, compound

Product 1

HCID 86713166HCID 86713166, compound

Procedure

The product of step 3 of Example 4 (10 mg, 0.025 mmol) is stirred with concentrated sulfuric acid (0.5 mL) at room temperature for 30 minutes. The solution is basified with saturated aqueous sodium bicarbonate (5 mL) and extracted with 10% methanol in CH2Cl2 (10 mL). The organics are concentrated and the residue purified by chromatography on a reverse phase C-18 column eluting with a gradient of neat water with 0.1% trifluoroacetic acid to neat acetonitrile with 0.1% trifluoroacetic acid to give the title compound (2 mg): m/z (Cl) 415 [M+H].

Workup

  1. extractionextracted with 10% methanol in CH2Cl2 (10 mL)
  2. concentrationThe organics are concentrated
  3. customthe residue purified by chromatography on a reverse phase C-18 column
  4. washeluting with a gradient of neat water with 0.1% trifluoroacetic acid to neat acetonitrile with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-3fb4aed9486a42938d2decad587cabe9
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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