Acetone → HCID 16048692, compound

HRID 1364143Notes

Reaction equation

HRID 1364143 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:22]=[C:21]4[C:15]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[N:14]3)=[CH:9][CH:8]=2)[C:3]1=[O:23].[CH3:24][C:25]([CH3:27])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:22]=[C:21]4[C:15]([CH2:16][CH2:17][N:18]([CH:25]([CH3:27])[CH3:24])[CH2:19][CH2:20]4)=[N:14]3)=[CH:9][CH:8]=2)[C:3]1=[O:23]

Participants

7

Reactant 3

HCID 180Acetone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 66930818HCID 66930818, compound

Product 1

HCID 16048692HCID 16048692, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-methyl-3-[4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]-2-imidazolidinone (may be prepared as described in Description 29) (44.0 mg, 0.14 mmol) in dichloromethane (3 ml) was treated with acetone (41 μl, 0.56 mmol) and acetic acid (1 drop) and stirred at room temperature. Sodium triacetoxyborohydride (60.0 mg, 0.28 mmol) was added and the mixture stirred for 3 hours and then overnight with a further portion of acetone and sodium triacetoxyborohydride added. The mixture was diluted with methanol and passed down a SCX cartridge eluting with methanol and then a 2M solution of ammonia in methanol. The basic fractions were combined and evaporated to afford the title compound (E10); MS (ES+) m/e 354 [M+H]+.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. washeluting with methanol
  3. customevaporated

Sources & evidence

ORD record
ord-bc06195d2b384601a5d72631b7e10e9c
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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