Sodium borohydride → HCID 59830888, compound

HRID 130948Notes

Reaction equation

HRID 130948 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:19]=[C:18]([F:20])[C:7]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][N:10]=2)=[C:6]([F:21])[CH:5]=1.[BH4-].[Na+]>CO>[F:21][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][CH2:2][CH2:3][CH:4]([CH3:19])[CH3:5])[CH:19]=[C:18]([F:20])[C:7]=1[O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59729971HCID 59729971, compound

Product 1

HCID 59830888HCID 59830888, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 3-methyl-butylaldehyde (26 μl, 0.24 mmol), amine from step 6 above and 3 A molecular sieves (900 mg) in methanol (3 mL), stir the mixture at room temperature overnight. Add NaBH4 (45 mg, 1.20 mmol) and stir at room temperature for 3 hours. Filtrate the mixture over celite and eliminate the solvent. Submit the crude to a SCX column to obtain a solid which was further purified by HPLC (Column: X-Terra MS C18. A=10 Mm NH4HCO3 pH8/B═CH3CN. Gradient mode: from 30 to 70% B. Flow rate: 1 mL/min) to obtain the title compound (42 mg). Electrospray MS M+1 ion=364. 1H-NMR (metanol-d4, 300 MHz): 8.60 (d, 1H, J=2.0 Hz), 8.32 (dd, 1H, J=2.2 and 8.5 Hz), 7.19 (d, 1H, J=8.7 Hz), 7.01-6.98 (m, 2H), 2.85 (m, 4H), 2.63 (m, 2H), 1.62 (m, 1H), 1.42 (q, 1H, J=7.3 Hz), 0.92 (d, 6H, J=6.5 Hz).

Workup

  1. customto obtain a solid which
  2. customwas further purified by HPLC (Column

Sources & evidence

ORD record
ord-779aec45a5a041d1897b927ccc66ef4c
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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