Ammonium Chloride → HCID 11420459, compound

HRID 2115294Notes

Reaction equation

HRID 2115294 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[Cl:12][C:13]1[C:14]([C:30]([F:33])([F:32])[F:31])=[N:15][N:16]([CH2:19][C:20]([N:22]2[CH2:29][CH:28]3[CH:24]([CH2:25][NH:26][CH2:27]3)[CH2:23]2)=[O:21])[C:17]=1[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:26]2[CH2:25][CH:24]3[CH2:23][N:22]([C:20](=[O:21])[CH2:19][N:16]4[C:17]([CH3:18])=[C:13]([Cl:12])[C:14]([C:30]([F:33])([F:31])[F:32])=[N:15]4)[CH2:29][CH:28]3[CH2:27]2)=[CH:4][C:3]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 129097254-Chloro-3-methoxybenzaldehydeHCID 59813964HCID 59813964, compound

Product 1

HCID 11420459HCID 11420459, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-3-methoxybenzaldehyde (34 mg) and compound 7 (35 mg) in THF (1 mL) was stirred at room temperature for 1 hour and then sodium triacetoxyborohydride (85 mg) was added in one portion. The mixture was stirred at room temperature for another hour and EtOAc (1 mL) was added followed by the addition of saturated aqueous ammonium chloride (1 mL). The aqueous phase was extracted by EtOAc (3×1 mL) and the combined organic extractants was dried, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to afford the title compound 8 as a white solid (36 mg, 95%). LCMS: Rf: 3.460 min, M+H+: 491.

Workup

  1. extractionThe aqueous phase was extracted by EtOAc (3×1 mL)
  2. customthe combined organic extractants was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a82f39e063ae4c02a4a688042e0e7d82
Source dataset
uspto-grants-2008_10
Patent number
US07435831B2

Reaction notes

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