Sulfuric Acid → HCID 58949528, compound

HRID 1676406Notes

Reaction equation

HRID 1676406 reaction equation
[C:1]([C:3]1[S:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[C:23](=[O:35])[N:24]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[N:25]=[CH:26][CH:27]=3)=[O:21])=[CH:15][C:14]=2[F:36])[CH:4]=1)#[N:2].[OH:37]S(O)(=O)=O>>[F:36][C:14]1[CH:15]=[C:16]([NH:19][C:20]([C:22]2[C:23](=[O:35])[N:24]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[N:25]=[CH:26][CH:27]=2)=[O:21])[CH:17]=[CH:18][C:13]=1[O:12][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:4]=[C:3]([C:1]([NH2:2])=[O:37])[S:11][C:10]=12

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67347435HCID 67347435, compound

Product 1

HCID 58949528HCID 58949528, compound

Procedure

A mixture of N-(4-(2-cyanothieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (Example 173, Step B, 10 mg, 0.02 mmol) and H2SO4 (0.53 mL, 9.97 mmol) was stirred at room temperature for 17 hours. The reaction mixture was quenched with ice. The mixture was treated with 2N NaOH, extracted with CH2Cl2 (500 mL) and DMF (40 mL), dried over MgSO4, and concentrated to afford the desired product which was rinsed with Et2O. LRMS (APCI pos) m/e 520.3 (M+1). 1H-NMR (400 MHz, DMSO-d6) δ 11.72 (s, 1H), 8.59 (d, 1H), 8.38 (d, 1H), 8.27 (m, 2H), 8.06 (d, 1H), 7.69 (m, 2H), 7.57 (m, 2H), 7.42 (t, 2H), 6.79 (d, 1H); 19F NMR (376 MHz, CDCl3/CD3OD) δ −112.9, −128.3.

Workup

  1. customThe reaction mixture was quenched with ice
  2. additionThe mixture was treated with 2N NaOH
  3. extractionextracted with CH2Cl2 (500 mL) and DMF (40 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e96244ee6fa40b984067526df066d3a
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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