Formaldehyde → HCID 9849390, compound

HRID 1531310Notes

Reaction equation

HRID 1531310 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:18][C:19]([C:21]3[C:22]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=3)=[O:20])[CH:15]=2)[CH2:10]1.[CH2:38](N(CC)CC)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH3:38])[CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:18][C:19]([C:21]3[C:22]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:33]=4)=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=3)=[O:20])[CH:15]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 9892231HCID 9892231, compound

Product 1

HCID 9849390HCID 9849390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid [2-(2-pyridylmethylamino)-indan-5-yl] amide (the compound of Example 20f, 0.4 g, 0.8 mmol) in methylene chloride (5 mL) is added triethylamine (0.12 g, 1.15 mmol) and paraformaldehyde (0.024 g, 0.8 mmol). The mixture is stirred for two hours and then sodium triacetoxyborohydride (0.24 g, 1.12 mmol) is added. The mixture is stirred overnight and then washed with dilute sodium bicarbonate, dried over sodium sulfate, and evaporated. The residue is purified by flash chromatography (SiO2; ethyl acetate) to afford 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid [2[(2-pyridylmethyl)(methyl)amino]-indan-5-yl] amide as a white solid, mp 105-115°.

Workup

  1. stirringThe mixture is stirred overnight
  2. washwashed with dilute sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by flash chromatography (SiO2; ethyl acetate)

Sources & evidence

ORD record
ord-d22c7a51ce0c4493ad91c303a53ebe0f
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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