Triethylamine → HCID 19003174, compound

HRID 2259297Notes

Reaction equation

HRID 2259297 reaction equation
[CH2:1]([N:3](CC)CC)C.[F:8][C:9]([F:45])([F:44])[C:10]1[CH:11]=[C:12]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:13][NH:14][C:15](=[O:36])[CH:16]([NH:27][C:28](=[O:35])C1C=CC=CC=1)[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.CN=C=O>O1CCCC1>[F:43][C:40]([F:42])([F:41])[C:38]1[CH:37]=[C:12]([CH:11]=[C:10]([C:9]([F:8])([F:44])[F:45])[CH:39]=1)[CH2:13][NH:14][C:15](=[O:36])[CH:16]([NH:27][C:28]([NH:3][CH3:1])=[O:35])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 19003177HCID 19003177, compound

Product 1

HCID 19003174HCID 19003174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.3 ml) was added to a stirred solution of the compound of Example 26 (1 g) in tetrahydrofuran (15 ml), at room temperature under a nitrogen atmosphere. After 5 minutes methyl isocyanate (0.13 ml) was added and the solution was stirred for 3 hours. The solvent was removed and the residue was dissolved in ethyl acetate (50 ml). The solution was washed with dilute hydrochloric acid, water and sodium bicarbonate solution. After drying over Na2SO4 removal of the solvent gave the title compound (0.9 g) after recrystallisation from ethyl acetate/petroleum ethereum ether, m.p. 213°-215° C. Found: C, 54.62; H, 4.28; N, 11.41. C22H20N4O2F6 requires C, 54.32; H, 4.14; N, 11.51.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washThe solution was washed with dilute hydrochloric acid, water and sodium bicarbonate solution
  4. dry with materialAfter drying over Na2SO4 removal of the solvent

Sources & evidence

ORD record
ord-5b5b1c2191c74f42a8ffbe1cf28c0d4d
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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