Acetic Acid → HCID 70498603, compound

HRID 1045494Notes

Reaction equation

HRID 1045494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])OC(C)(C)C)[C:3]=1[CH:16]=O.[NH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].CC(O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[CH:16]3[N:22]([C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:29])[CH2:21][CH2:20][CH2:19][N:18]3[C:9](=[O:15])[NH:8][C:4]=2[N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 46204204tert-Butyl 4-chloro-3-formylpyridin-2-ylcarbamate

Product 1

HCID 70498603HCID 70498603, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (4-chloro-3-formylpyridin-2-yl)carbamate (1.2 g, 4.67 mmol), tert-butyl (3-amino-propyl)carbamate (855 mg, 4.91 mmol), and AcOH (0.28 g, 4.67 mmol) were suspended in toluene (50 mL), and stirred overnight at room temperature. The reaction mixture was concentrated. The crude intermediate was dissolved in NMP (8 mL) in a 40 mL sealed tube, and stirred for 30 min. at 160 ° C. The reaction mixture was cooled, and the resulting precipitate was filtered, washed with MeOH, and dried under vacuum. LC-MS (M+H=339, obsd.=339).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe crude intermediate was dissolved in NMP (8 mL) in a 40 mL
  3. customsealed tube
  4. stirringstirred for 30 min. at 160 ° C
  5. temperatureThe reaction mixture was cooled
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with MeOH
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2ff31f22f3b14146a229ca6c12cdc2f6
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

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