Sodium triacetoxyborohydride → HCID 57677428, compound

HRID 492798Notes

Reaction equation

HRID 492798 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([NH:25][C:26]([NH:28][C:29](=[O:37])[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[S:27])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1.Cl.[NH:39]1[CH2:42][CH2:41][CH2:40]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:39]1([CH:17]2[CH2:18][CH2:19][N:14]([C:12]([NH:11][C:7]3[CH:6]=[C:5]([O:4][C:3]4[CH:21]=[CH:22][C:23]([NH:25][C:26]([NH:28][C:29](=[O:37])[CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[S:27])=[CH:24][C:2]=4[F:1])[CH:10]=[CH:9][N:8]=3)=[O:13])[CH2:15][CH2:16]2)[CH2:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 57677483HCID 57677483, compound

Product 1

HCID 57677428HCID 57677428, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{2-fluoro-4-[3-(2-phenylacetyl)thioureido]phenoxy}-2-[(4-oxopiperidin-1-yl)carbonylamino]pyridine (38 mg) in dichloromethane (2.0 ml) were added azetidine hydrochloride (17 mg) and sodium triacetoxyborohydride (40 mg) at room temperature, followed by stirring overnight. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=95:5). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was dried in vacuum to provide the titled compound (31.9 mg, 78%) as white powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=95:5)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated under a reduced pressure
  9. customto give a residue, which
  10. customwas dried in vacuum

Sources & evidence

ORD record
ord-3d9cb692f33a4b709f15954be208e07b
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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