Acetic Acid → HCID 59134262, compound

HRID 1994413Notes

Reaction equation

HRID 1994413 reaction equation
[C:1](O)(=O)C.C=O.C([BH3-])#N.[Na+].[Cl:11][C:12]1[CH:52]=[CH:51][C:15]([CH2:16][CH:17]2[N:22]3[C:23](=[O:46])[CH:24]([NH:38][C:39]([CH:41]4[CH2:45][CH2:44][CH2:43][NH:42]4)=[O:40])[CH2:25][N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])(=[O:29])=[O:28])[CH:21]3[CH2:20][N:19]([CH:47]([CH3:49])[CH3:48])[C:18]2=[O:50])=[CH:14][CH:13]=1>CO>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[N:22]3[C:23](=[O:46])[CH:24]([NH:38][C:39]([CH:41]4[CH2:45][CH2:44][CH2:43][N:42]4[CH3:1])=[O:40])[CH2:25][N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])(=[O:29])=[O:28])[CH:21]3[CH2:20][N:19]([CH:47]([CH3:49])[CH3:48])[C:18]2=[O:50])=[CH:51][CH:52]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59134101HCID 59134101, compound

Product 1

HCID 59134262HCID 59134262, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.3 ml (5.2 mmol) of acetic acid, 0.25 ml (3.33 mmol) of formaldehyde (37% in water) and 1.5 ml (1.5 mmol) of sodium cyanoborohydride (1M in THF) were added to a solution of 93 mg (0.142 mmol) of the amine from Example 40 in 7.5 ml of methanol. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was diluted with 10 ml of DCM, basified with 7N—NH3 in methanol, filtered and concentrated. This residue was purified by preparative RP-HPLC. 50 mg of the desired compound were obtained. LC/MS (calculated, monoisotopic MW=669; measured value (M+H)=670)

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 10 ml of DCM
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThis residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-486a101f064f4e9ba96c5c197534642f
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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