Triethylamine → HCID 14013073, compound

HRID 1904855Notes

Reaction equation

HRID 1904855 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[N:22]([CH2:23][C:24]3[O:25][CH:26]=[CH:27][CH:28]=3)[C:21]3[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=3[N:19]=2)[CH2:13][CH2:12]1)=[O:5].C(N(CC)CC)C.[C:44](Cl)(=O)[O:45]C(Cl)(Cl)Cl>O1CCCC1>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[CH2:23][N:22]1[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[N:19]=[C:18]1[CH2:17][CH:14]1[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:1][C:44]2=[O:45])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 14013066HCID 14013066, compound

Product 1

HCID 14013073HCID 14013073, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3.88 parts of 2-amino-N-[4-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]butyl]benzamide, 2 parts of N,N-diethylethanamine and 90 parts of tetrahydrofuran were added dropwise 1.64 parts of trichloromethyl carbonochloridate. Upon completion, stirring was continued overnight. Another portion of 1.6 parts of B was added and the whole was stirred overnight. The precipitate was filtered off and the filtrate was evaporated. Water was added to the residue. The solution was treated with ammonium hydroxide; The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 3 parts (73%) of 3-[4-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione; mp. 185.5° C. (490).

Workup

  1. additionAnother portion of 1.6 parts of B was added
  2. stirringthe whole was stirred overnight
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate was evaporated
  5. additionWater was added to the residue
  6. additionThe solution was treated with ammonium hydroxide
  7. extractionThe product was extracted with dichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-a8dd60f878144a85a8652d312eb3fb23
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

Loading…