Formaldehyde → HCID 68827109, compound

HRID 2101423Notes

Reaction equation

HRID 2101423 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[CH:4][CH:3]=1.[C:33]([NH2:41])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C=O.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:33])[C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[CH:4][CH:3]=1.[C:33]([NH2:41])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 68826459HCID 68826459, compound

Product 1

HCID 68827109HCID 68827109, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title benzamide from Example 1 (21 mg) was dissolved in THF prior to the addition of Hunigs's base (0.01 mL). Next, 37% formaldehyde (0.017 mL) was added along with 4A molecular sieves. After 3 h, NaHB(OAc)3 (38 mg) was added. This mixture was stirred an additional 2 h before the reaction was quenched-with NaHCO3 solution. This was extracted with EtOAc. The EtOAc was dried and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide N-[2-[[(1S,2S)-2-[(4-chlorobenzyl)(methyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide (10 mg). MS found: (M+H)+=482.3.

Workup

  1. extractionThis was extracted with EtOAc
  2. dry with materialThe EtOAc was dried
  3. concentrationconcentrated
  4. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Sources & evidence

ORD record
ord-1d3a9bf998384e87955f1efeb29694eb
Source dataset
uspto-grants-2009_08
Patent number
US07572813B2

Reaction notes

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