Acetic Acid → HCID 21054829, compound

HRID 2376898Notes

Reaction equation

HRID 2376898 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([NH:29][CH2:30][CH3:31])=[O:28])[CH:21]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[O:9])[CH2:3][CH2:2]1.C=O.[C:34](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.CO>[CH3:34][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([NH:29][CH2:30][CH3:31])=[O:28])[CH:21]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[O:9])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21054831HCID 21054831, compound

Product 1

HCID 21054829HCID 21054829, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-(3-Ethylureido)pyridin-4-yloxy)indole-1-carboxylic acid piperidin-4-ylamide (36 mg, 0.085 mmol, Example 181) was dissolved in tetrahydrofuran (2.0 ml) and methanol (1.0 ml); and a 37% aqueous formaldehyde solution (0.036 ml, 0.43 mmol) and acetic acid (0.0098 ml, 0.17 mmol) were added thereto. While stirring at room temperature, sodium triacetoxyborohydride (27 mg, 0.13 mmol) was added; and the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; the obtained crystals were suspended in diethyl ether, filtered off, washed with diethyl ether, and dried to yield the title compound (25 mg, 0.057 mmol, 67%) as colorless crystals.

Workup

  1. stirringand the reaction mixture was stirred for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washand the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. filtrationfiltered off
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-5b4c9e486b214bf6823025794c56ae83
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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