Acetone → HCID 131728090, compound

HRID 645663Notes

Reaction equation

HRID 645663 reaction equation
[CH3:1][C:2]([CH3:4])=O.[C:5]([OH:8])(=[O:7])[CH3:6].[C:9]([OH:12])(=[O:11])[CH3:10].[N:13]1([C:20]2[C:25]([CH2:26][NH:27][C:28]3[N:32]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[C:35]([Cl:40])[C:34]=4[Cl:41])[N:31]=[N:30][N:29]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:5]([OH:8])(=[O:7])[CH3:6].[C:9]([OH:12])(=[O:11])[CH3:10].[Cl:41][C:34]1[C:35]([Cl:40])=[C:36]([F:39])[CH:37]=[CH:38][C:33]=1[N:32]1[C:28]([NH:27][CH2:26][C:25]2[C:20]([N:13]3[CH2:19][CH2:18][CH2:17][N:16]([CH:2]([CH3:4])[CH3:1])[CH2:15][CH2:14]3)=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:29][N:30]=[N:31]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 131728089HCID 131728089, compound

Product 1

HCID 131728090HCID 131728090, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Acetone (0.5 mL) was added to a mixture of the product of Example 289 (80 mg, 0.183 mmol) and sodium triacetoxyborohydride (77 mg, 0.366 mmol) in 1,2-dichloroethane (5 mL). The reaction mixture was stirred at room temperature overnight. The mixture was filtered and washed with dichloromethane. The filtrate was concentrated under reduced pressure and purified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size) using a gradient of 5% to 75% acetonitrile to ammonium acetate (10 mM) over 20 minutes at a flow rate of 21 mL/min to provide the title compound. MS (ESI+) m/z 479.3 (M+H)+; Rt=1.63 min. 1H-NMR (400 MHz, DMSO-d6) δ 0.96 (d, J=6.6 Hz, 1H), 1.80 (m, 2H), 1.90 (s, 2H), 2.65 (m, 2H), 2.70 (m, 2H), 2.86 (m, 1H), 3.38 (m, 4H), 4.44 (d, J=5.3 Hz, 1H), 5.75 (s, 1H), 6.84 (dd, J=4.8 Hz, J=7.5 Hz, 1H), 7.52 (dd, J=1.9 Hz, J=7.5 Hz, 1H), 7.58 (t, J=5.5 Hz, 1H), 7.73 (t, J=8.8 Hz, 1H), 7.86 (dd, J=5.3 Hz, J=9.0 Hz, 1H), 8.07 (dd, J=1.9 Hz, J=4.7 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size)
  5. customover 20 minutes

Sources & evidence

ORD record
ord-72bfc39274ed4ba487b05b9f74ac7750
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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