Acetic Acid → HCID 90413388, compound

HRID 1522042Notes

Reaction equation

HRID 1522042 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:16][C:9]=23)[C:5]([Cl:30])=[CH:4][N:3]=1.[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH:35]=O.C(O)(=O)C>ClCCl>[Cl:30][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]4)=[CH:16][C:9]=23)=[CH:7][C:2]([NH:1][CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[C:32]([F:31])[CH:33]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 680093-FluorobenzaldehydeHCID 90412802HCID 90412802, compound

Product 1

HCID 90413388HCID 90413388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 307A (74 mg, 0.17 mmol) and 3-fluorobenzaldehyde (107 mg, 0.86 mmol) in dichloromethane was added acetic acid (0.05 mL, 0.86 mmol) and MP-CNBH3 (2.49 mmol/g) (278 mg, 0.69 mmol). The mixture was stirred overnight and the insoluble material was filtered off. The filtrated was concentrated. The residue was purified by flash chromatograph eluting with a gradient of 10%-50% ethyl acetate in hexanes to provide the title compound. LCMS: 537 (M+H)+.

Workup

  1. filtrationthe insoluble material was filtered off
  2. concentrationThe filtrated was concentrated
  3. customThe residue was purified by flash chromatograph
  4. washeluting with a gradient of 10%-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-de8e1ec80e34402d81356ef44e13add1
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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