Acetic Acid → HCID 10162183, compound

HRID 8277Notes

Reaction equation

HRID 8277 reaction equation
N[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[N:22][N:21]4[CH2:31][CH2:32][CH2:33][C:20]=34)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:5])[CH3:4].[C:34]([BH3-])#[N:35].[Na+].[C:38](O)(=O)C.C=O>CO>[CH3:38][N:35]([CH3:34])[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[N:22][N:21]4[CH2:31][CH2:32][CH2:33][C:20]=34)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 219926594-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid(2-amino-1,1-dimethyl-ethyl)-amide

Product 1

HCID 10162183HCID 10162183, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid(2-amino-1,1-dimethyl-ethyl)-amide (0.12 g, 0.27 mmol), sodium cyanoborohydride (0.038 g, 0.6 mmol), and acetic acid (0.077 mL, 1.3 mmol) in methanol (5 mL) is cooled to 0° C. and stirred for 10 min. A solution of 37% aqueous formaldehyde (0.086 mL, 3.1 mmol) in methanol (2 mL) is added dropwise. The mixture is allowed to warm to room temperature and stirred for 1 h. The reaction is quenched with saturated aqueous potassium carbonate solution and concentrated in vacuo. The residue is taken up in chloroform, washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue is chromatographed on SiO2 (8% methanol/92% dichloromethane) to yield the title compound, 33 mg (27%), as a white foam.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction is quenched with saturated aqueous potassium carbonate solution
  4. concentrationconcentrated in vacuo
  5. washwashed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on SiO2 (8% methanol/92% dichloromethane)

Sources & evidence

ORD record
ord-299b9a551a6048d98adae389038ab081
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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