Formaldehyde → HCID 56600993, compound

HRID 1619596Notes

Reaction equation

HRID 1619596 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]([C:10]3[CH:11]=[C:12]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:40]([F:43])([F:42])[F:41])[CH:13]=[CH:14][C:15]=3[O:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([S:24]([NH:27][C:28]4[S:29][CH:30]=[N:31][N:32]=4)(=[O:26])=[O:25])=[C:19]([F:33])[CH:18]=3)=[CH:8][CH:7]=[N:6]2)[CH2:2]1.C=O.[C:46](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.ClCCl.C(O)(=O)C>[Cl:23][C:22]1[C:17]([O:16][C:15]2[CH:14]=[CH:13][C:12]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:42])([F:43])[F:41])=[CH:11][C:10]=2[C:9]2[N:5]([CH:3]3[CH2:2][N:1]([CH3:46])[CH2:4]3)[N:6]=[CH:7][CH:8]=2)=[CH:18][C:19]([F:33])=[C:20]([S:24]([NH:27][C:28]2[S:29][CH:30]=[N:31][N:32]=2)(=[O:26])=[O:25])[CH:21]=1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58042299HCID 58042299, compound

Product 1

HCID 56600993HCID 56600993, compoundYield 132.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-{[3-(1-azetidin-3-yl-1H-pyrazol-5-yl)-2′-(trifluoromethyl)biphenyl-4-yl]oxy}-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 46, 42.9 mg, 0.0659 mmol) in methanol (0.10 mL), dichloromethane (1.72 mL) and acetic acid (0.10 mL) was added formaldehyde (37% w/w, 16.7 μL, 0.224 mmol). The reaction was then stirred under nitrogen at room temperature for 45 minutes. Sodium triacetoxyborohydride (42.6 mg, 0.201 mmol) was added to the reaction which was stirred for 18 hours at room temperature. The reaction was diluted with dichloromethane (20 mL) and washed with water (3×2 mL). The combined aqueous phases were extracted with dichloromethane (3×5 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a white solid (58.0 mg). The solid was purified by B-HPLC to afford the title compound.

Workup

  1. stirringwas stirred for 18 hours at room temperature
  2. washwashed with water (3×2 mL)
  3. extractionThe combined aqueous phases were extracted with dichloromethane (3×5 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ddb1ceac9164cbb99b8ea1dc08d497d
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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