Triethylamine → HCID 57500364, compound

HRID 2273537Notes

Reaction equation

HRID 2273537 reaction equation
C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:35]([O:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42]([OH:44])=O)(=[O:37])[CH3:36].[NH2:48][C:49]1[CH:58]=[CH:57][C:56]([C:59]([C:61]2[N:69]3[C:64]([CH:65]=[CH:66][CH:67]=[CH:68]3)=[C:63]([NH2:70])[C:62]=2[CH3:71])=[O:60])=[CH:55][C:50]=1[C:51]([O:53][CH3:54])=[O:52]>CN(C)C=O.C(OCC)(=O)C.CC(C)=O>[C:35]([O:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42]([NH:70][C:63]1[C:62]([CH3:71])=[C:61]([C:59]([C:56]2[CH:57]=[CH:58][C:49]([NH2:48])=[C:50]([CH:55]=2)[C:51]([O:53][CH3:54])=[O:52])=[O:60])[N:69]2[C:64]=1[CH:65]=[CH:66][CH:67]=[CH:68]2)=[O:44])(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2386693-Acetoxybenzoic acidHCID 57500365HCID 57500365, compound

Product 1

HCID 57500364HCID 57500364, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.95 ml (6.80 mmol) of triethylamine and 1.50 g (3.40 mmol) of BOP are added, at ambient temperature, to 0.61 g (3.40 mmol) of 3-acetoxybenzoic acid in suspension in 20 ml of N,N-dimethylformamide. After 15 minutes, 1.0 g (3.09 mmol) of methyl 2-amino-5-[(1-amino-2-methylindolizin-3-yl)carbonyl]benzoate (described in Patent Application WO2003084956) in 10 ml of N,N-dimethylformamide is added. The reaction medium is stirred for 16 hours under argon and then diluted with ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The solid obtained is taken up in acetone and then filtered and dried. 0.86 g (57%) of a greenish yellow powder is obtained.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-48721f5922024a1da030af0e619f1eef
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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