Acetic Acid → HCID 68108916, compound

HRID 1623810Notes

Reaction equation

HRID 1623810 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:16]([CH:26]=1)[C:17]([NH:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[O:18])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:29]1([CH2:28][O:27][C:15]2[CH:14]=[CH:13][C:12]([CH2:10][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:26][C:16]=2[C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86668210HCID 86668210, compound

Product 1

HCID 68108916HCID 68108916, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Pyrrolidine (25 uL, 0.30 mmol) and acetic acid (17 uL, 0.30 mmol) were added to a solution of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 100 mg, 0.30 mmol) in DCE (5 ml). The solution was stirred for 4 hours at 50° C. then sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added. The reaction was stirred overnight then quenched with NaHCO3 solution (7 ml) and extracted with dichloromethane (5 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a yellow solid. The residue purified by MDAP to yield the title compound as an opaque solid. 34 mg.

Workup

  1. stirringThe reaction was stirred overnight
  2. customthen quenched with NaHCO3 solution (7 ml)
  3. extractionextracted with dichloromethane (5 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a yellow solid
  7. customThe residue purified by MDAP

Sources & evidence

ORD record
ord-ec395945cc7c4f9986cf23710a99edcf
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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