Sodium Hydroxide → HCID 53239586, compound

HRID 1898162Notes

Reaction equation

HRID 1898162 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:3]=1[C:4]([C:6]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:27])=[CH:8][N:7]=1)=O.[Si]([N:37]=[C:38]=[O:39])(C)(C)C.[OH-].[Na+]>C1COCC1.CC(O)=O.CO>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][C:11]2[C:6]([CH:4]3[C:3]4[C:2](=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:32])[NH:1][C:38](=[O:39])[NH:37]3)=[N:7][CH:8]=[C:9]([Cl:27])[CH:10]=2)(=[O:14])=[O:15])=[CH:17][C:18]=1[C:23]([F:26])([F:25])[F:24]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 70696Trimethylsilyl isocyanateHCID 57942158HCID 57942158, compound

Product 1

HCID 53239586HCID 53239586, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

N-(2-(2-Amino-6-chlorobenzoyl)-5-chloro-pyridin-3-yl)-4-chloro-3-(trifluoromethyl)benzenesulfonamide (26 mg, 0.05 mmol) in THF (2 mL) was treated with TMS-isocyanate (100 mg) and AcOH (0.5 mL) and then stirred at 75° C. for 12 h. To the mixture was added MeOH (0.5 mL), followed by NaOH (5 N, 1 mL), and the resultant mixture stirred at 75° C. for another 2 h. To the mixture was added AcOH (0.5 mL), and the mixture was purified through HPLC and dried (lyophilizer) to afford the title compound: 1H NMR (400 MHz, CDCl3) δ 8.82 (s, 2H), 8.34 (d, 1H), 8.14 (d, 1H), 7.90 (dd, 1H), 7.66 (d, 1H), 7.46 (s, 1H), 7.16 (t, 1H), 6.90 (d, 2H), 6.81 (d, 1H), 6.14 (d, 1H); MS (ES) (M+H)+ expected 550.9. found 550.9.

Workup

  1. customthe mixture was purified through HPLC
  2. customdried (lyophilizer)

Sources & evidence

ORD record
ord-c9f56cdef60043739c47649fcfd974dd
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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