Formaldehyde → HCID 57494824, compound

HRID 1692217Notes

Reaction equation

HRID 1692217 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]([C:10]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:11]=3[O:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([S:20]([NH:23][C:24]4[N:25]=[CH:26][S:27][CH:28]=4)(=[O:22])=[O:21])=[C:15]([F:29])[CH:14]=3)=[CH:8][CH:7]=[N:6]2)[CH2:2]1.CO.C=O.[C:39](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:19][C:18]1[C:13]([O:12][C:11]2[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:10]=2[C:9]2[N:5]([CH:3]3[CH2:4][N:1]([CH3:39])[CH2:2]3)[N:6]=[CH:7][CH:8]=2)=[CH:14][C:15]([F:29])=[C:16]([S:20]([NH:23][C:24]2[N:25]=[CH:26][S:27][CH:28]=2)(=[O:21])=[O:22])[CH:17]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 46841354HCID 46841354, compound

Product 1

HCID 57494824HCID 57494824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(1-Azetidin-3-yl-1H-pyrazol-5-yl)-4-fluorophenoxy]-5-chloro-2-flouro-N-1,3-thiazol-4-ylbenzenesulfonamide (Example 808, 29 mg, 0.052 mmol) was stirred in dichloromethane (2 ml), methanol (0.2 ml), aqueous formaldehyde (0.015 ml of 37% wt/vol) added and the reaction stirred at room temperature for a further 30 minutes. Sodium triacetoxyborohydride (37 mg, 0.172 mmol) was added and the solution stirred for 3 hours. The solvents were removed in vacuo and the residue dissolved in ethyl acetate and extracted with saturated aqueous sodium hydrogencarbonate solution (2×10 ml) and brine (2×10 ml). The organic layer was separated, dried over sodium sulphate, filtered and evaporated to give a solid. The compound was purified using preparative HPLC to afford the title compound. Yield 15.9 mg 57%.

Workup

  1. stirringthe solution stirred for 3 hours
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. extractionextracted with saturated aqueous sodium hydrogencarbonate solution (2×10 ml) and brine (2×10 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a solid
  10. customThe compound was purified

Sources & evidence

ORD record
ord-eabb7bcadf9349e9b09cae9cb7564151
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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