4-Fluorobenzylamine → HCID 86673116, compound

HRID 1853355Notes

Reaction equation

HRID 1853355 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=O)[CH:15]=2)[O:10][C:9]([C:19]2[N:24]=[CH:23][N:22]3[CH:25]=[CH:26][CH:27]=[C:21]3[CH:20]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][NH:34][CH2:33][C:32]3[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=3)[CH:15]=2)[O:10][C:9]([C:19]2[N:24]=[CH:23][N:22]3[CH:25]=[CH:26][CH:27]=[C:21]3[CH:20]=2)=[CH:8]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86673117HCID 86673117, compound

Product 1

HCID 86673116HCID 86673116, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-Butoxyimino-2-pyrrolo[1,2-c]pyrimidin-3-yl-4H-chromene-6-carbaldehyde (example 144B) (50 mg; 0.14 mmol) in dichloromethane (5 ml), was added molecular sieves and 4-Fluoro-benzylamine (19 mg; 0.15 mmol). After 2 hours at room temperature, sodium triacetoxyborohydride (29 mg, 0.14 mmol) and acetique acid (2 ml), were added. After stirring at room temperature for 18 hours, the reaction mixture was quenched with a saturated solution of sodium hydrogenocarbonate and extracted with ethyl acetate. The organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-100%) to afford the title compound (20 mg, 30%) as a green solid.

Workup

  1. customthe reaction mixture was quenched with a saturated solution of sodium hydrogenocarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-100%)

Sources & evidence

ORD record
ord-12adabd96abe43aaa985b423e733e385
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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