Sulfuric Acid → HCID 178428294, compound

HRID 1503875Notes

Reaction equation

HRID 1503875 reaction equation
[C:1]([C:3]1[C:4]2[N:42](COCC[Si](C)(C)C)[CH:41]=[N:40][C:5]=2[C:6]([CH2:31][C:32]2[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:39])=[N:7][C:8]=1[NH:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[C:12]([CH3:30])[CH:11]=1)#[N:2].S(=O)(=O)(O)[OH:52]>O>[Cl:38][C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:39])[C:32]=1[CH2:31][C:6]1[C:5]2[N:40]=[CH:41][NH:42][C:4]=2[C:3]([C:1]([NH2:2])=[O:52])=[C:8]([NH:9][C:10]2[CH:11]=[C:12]([CH3:30])[C:13]([N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:14][C:15]=2[F:16])[N:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86725409HCID 86725409, compound

Product 1

HCID 178428294HCID 178428294, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To the product of Example 51D (190 mg, 0.26 mmol) at 0° C. was added concentrated sulfuric acid (3 mL) and water (0.6 mL) and the mixture was heated at 90° C. for 20 minutes. After quenching with water (20 mL) and adjusting to pH 8 with saturated sodium bicarbonate solvent, the mixture was extracted with 4/1 dichloromethane/methanol (3×100 mL). The organic layers were collected, 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 13.63 (s, 1H), 11.98 (s, 1H), 9.63 (s, 1H), 8.64 (m, 3H), 7.90 (d, 1H), 7.83 (s, 1H), 7.56 (d, 2H), 7.39 (t, 1H), 6.90 (d, 1H), 4.74 (s, 2H), 3.25 (m, 4H), 2.95 (m, 4H), 2.07 (s, 3H). MS: 528 (M+H+).

Workup

  1. customAfter quenching with water (20 mL)
  2. extractionthe mixture was extracted with 4/1 dichloromethane/methanol (3×100 mL)
  3. customThe organic layers were collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d9b1410efa964ad7bfb9b5a0c1378763
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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