Sodium borohydride → HCID 21104611, compound

HRID 1354205Notes

Reaction equation

HRID 1354205 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([CH:12]=O)[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[NH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH:23]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]=[CH:27][CH:26]=2)[OH:24])[CH2:17]1.[BH4-].[Na+]>CO.ClCCl>[OH:24][CH:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][CH:26]=1)[CH2:22][N:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([CH2:15][NH:14][CH2:12][C:9]2[CH:10]=[CH:11][C:5]3[O:4][CH2:3][C:2](=[O:1])[NH:7][C:6]=3[CH:8]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeHCID 21104608HCID 21104608, compound

Product 1

HCID 21104611HCID 21104611, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Molecular sieve, type 3A, (1.082 g) and 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.095 g, 0.54 mmol) were added to a solution of (3S)-2-(3-aminomethyl-piperidin-1-yl)-1-(6-methoxy-quinolin-4-yl)-ethanol (0.171 g, 0.54 mmol) in MeOH (1.6 ml) and dichloromethane (3.8 ml). The reaction mixture was stirred at room temperature for 16 hours and sodium borohydride (0.054 g, 1.43 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 1% NH4OH).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. filtrationfiltered over Hydromatrix (
  3. washsubsequently washed with dichloromethane
  4. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 1% NH4OH)

Sources & evidence

ORD record
ord-5f38059a67f647dc8b1faf166a3e2dc7
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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