Sulfuric Acid → HCID 178492703, compound

HRID 1503850Notes

Reaction equation

HRID 1503850 reaction equation
[C:1]([C:3]1[C:4]2[N:37](COCC[Si](C)(C)C)[CH:36]=[N:35][C:5]=2[C:6]([CH2:26][C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])=[N:7][C:8]=1[NH:9][C:10]1[CH:23]=[CH:22][C:13]([C:14]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:15])=[CH:12][C:11]=1[O:24][CH3:25])#[N:2].S(=O)(=O)(O)[OH:47]>O>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[CH2:26][C:6]1[C:5]2[N:35]=[CH:36][NH:37][C:4]=2[C:3]([C:1]([NH2:2])=[O:47])=[C:8]([NH:9][C:10]2[CH:23]=[CH:22][C:13]([C:14](=[O:15])[NH:16][CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])=[CH:12][C:11]=2[O:24][CH3:25])[N:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70562886HCID 70562886, compound

Product 1

HCID 178492703HCID 178492703, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of Example 31C (60 mg, 0.1 mmol) in concentrated sulfuric acid (3 mL) and water (0.5 mL) was stirred for 10 minutes at 0° C. and at 90° C. for 1.5 hours. The mixture was quenched with crushed ice and adjusted pH 9 with sodium bicarbonate solution. The precipitate was filtered off and the filtrate was extracted with 4/1 dichloromethane/methane (5×50 mL). The organic layers were collected, concentrated and purified by preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 12.2 (s, 1H), 9.59 (s, 1H), 9.38 (s, 1H), 8.58-8.62 (d, J=12 Hz, 2H), 7.88-7.92 (m, 2H), 7.59-7.62 (m, 2H), 7.39-7.47 (m, 2H), 7.06 (m, 2H), 4.75 (s, 2H), 3.89 (s, 3H), 3.58-3.60 (d, J=6 Hz, 2H), 3.25-3.27 (d, J=6 Hz, 2H), 3.88 (s, 6H). MS: 556 (M+H+).

Workup

  1. customThe mixture was quenched with crushed ice and adjusted pH 9 with sodium bicarbonate solution
  2. filtrationThe precipitate was filtered off
  3. extractionthe filtrate was extracted with 4/1 dichloromethane/methane (5×50 mL)
  4. customThe organic layers were collected
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-fe79ccd0277248c0a60924c1f3f40659
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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