Acetone → HCID 11419193, compound

HRID 1243141Notes

Reaction equation

HRID 1243141 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([NH:23][C:24](=[O:27])[CH2:25][NH2:26])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)[CH3:2].[CH3:30][C:31]([CH3:33])=O.[BH3-]C#N.[Na+].C(OCC)(=O)C>CO>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2([NH:23][C:24](=[O:27])[CH2:25][NH:26][CH:31]([CH3:33])[CH3:30])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:8][CH:9]=1)[CH3:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 86596120HCID 86596120, compound

Product 1

HCID 11419193HCID 11419193, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The amine from Example 13A was dissolved in 1 M pH4 MeOH buffer (82 g NaOAc/L MeOH, add HOAc to pH 4.5) and acetone (12 mg, 0.2 mmol) and NaBH3CN (13 mg, 0.2 mmol) were added. Following stirring for 2 hours ethyl acetate (30 mL) was added and the resulting solution was washed with aqueous NaOH (1N, 2×10 mL). The organic phase was dried over MgSO4, concentrated, and purified by HPLC to provide the titled compound (30 mg, 23% over 3 steps). 1H NMR (300 MHz, DMSO-D6) δ 9.21 (s, 1H), 7.83 (s, 1H), 7.32 (d, J=9.3 Hz, 2H), 7.10 (m, 4H), 6.61 (d, J=9.0 Hz, 2H), 3.28 (q, J=6.9 Hz, 4H), 3.22 (d, J=18.9 Hz, 1H), 3.11 (d, J=18.9 Hz, 1H), 3.07 (s, 2H), 2.77 (m, 2H), 2.45 (m, 2H), 2.09 (m, 1H), 1.05 (t, J=7.2 Hz, 6H), 0.81 (d, J=6.3 Hz, 3H), 0.73 (d, J=6.3 Hz, 6H). MS (ESI) positive ion 437 (M+H)+; negative ion 435 (M−H)−.

Workup

  1. additionwas added
  2. washthe resulting solution was washed with aqueous NaOH (1N, 2×10 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-778816159bb940c7b6fc739255ab629b
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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