Ammonia → HCID 68921730, compound

HRID 1987839Notes

Reaction equation

HRID 1987839 reaction equation
C([N:3](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.[CH3:35][O:36][C:37]1[C:38]([CH3:62])=[C:39]([C:49](=[O:61])[C:50]2[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[C:52]([O:59][CH3:60])[CH:51]=2)[N:40]2[C:45]=1[CH:44]=[CH:43][C:42]([C:46](O)=[O:47])=[CH:41]2.N.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.C(OC(C)C)(C)C.O>[CH3:35][O:36][C:37]1[C:38]([CH3:62])=[C:39]([C:49](=[O:61])[C:50]2[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[C:52]([O:59][CH3:60])[CH:51]=2)[N:40]2[C:45]=1[CH:44]=[CH:43][C:42]([C:46]([NH2:3])=[O:47])=[CH:41]2

Participants

10

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 68849354HCID 68849354, compound

Product 1

HCID 68921730HCID 68921730, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

104 μl (0.74 mmol) of triethylamine and then 330 mg (0.74 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) are added to 260 mg (0.66 mmol) of [1-methoxy-3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-6-yl]carboxylic acid in 5 mL of N,N-dimethylformamide and the medium is stirred for one hour at room temperature. 0.9 mL (2.71 mmol) of a 3N solution of ammonia in tetrahydrofuran is added to the reaction medium and the medium is kept stirred at room temperature overnight. Water and a saturated aqueous sodium bicarbonate solution are added. The medium is extracted several times with ethyl acetate. The organic phase is separated by decantation, dried over sodium sulfate and concentrated under vacuum. The solid residue obtained is taken up in isopropyl ether, filtered, washed with isopropyl ether and then dried. 210 mg of a red solid are obtained.

Workup

  1. stirringthe medium is kept stirred at room temperature overnight
  2. extractionThe medium is extracted several times with ethyl acetate
  3. customThe organic phase is separated by decantation
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe solid residue obtained
  7. filtrationfiltered
  8. washwashed with isopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-6860d6dda7eb411d8f44233515a7386a
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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