Ammonium Chloride → HCID 56597648, compound

HRID 409554Notes

Reaction equation

HRID 409554 reaction equation
[Cl-].[NH4+].[B-](F)(F)(F)F.CCOC(C(C#N)=[N:14]OC(N(C)C)=[N+](C)C)=O.C(N(CC)C(C)C)(C)C.[CH3:34][C:35]1[N:44]([CH2:45][CH2:46][CH3:47])[C:43](=[O:48])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:49]([C:51]3[N:55]4[CH:56]=[CH:57][CH:58]=[CH:59][C:54]4=[C:53]([C:60]4[CH:61]=[C:62]([CH:66]=[CH:67][CH:68]=4)[C:63]([OH:65])=O)[N:52]=3)=[O:50])[CH:41]=2)[N:36]=1>CN(C=O)C>[CH3:34][C:35]1[N:44]([CH2:45][CH2:46][CH3:47])[C:43](=[O:48])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:49]([C:51]3[N:55]4[CH:56]=[CH:57][CH:58]=[CH:59][C:54]4=[C:53]([C:60]4[CH:61]=[C:62]([CH:66]=[CH:67][CH:68]=4)[C:63]([NH2:14])=[O:65])[N:52]=3)=[O:50])[CH:41]=2)[N:36]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 56597647HCID 56597647, compound

Product 1

HCID 56597648HCID 56597648, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.107 g (2 mmol) of ammonium chloride, 0.328 g (1 mmol) of TOTU and 0.517 g (4 mmol) of N,N-diisopropylethylamine are added, at ambient temperature under an inert atmosphere, to 0.233 g (0.5 mol) of 3-{3-[(2-methyl-4-oxo-3-propyl-3,4-dihydroquinazolin-6-yl)carbonyl]imidazo[1,5-a]pyridin-1-yl}benzoic acid in 30 ml of DMF. The reaction medium is stirred for 5 hours at ambient temperature and then concentrated under reduced pressure. 50 ml of a saturated solution of sodium hydrogen carbonate are added to the residue. The precipitate obtained is filtered off, and then dried under reduced pressure at 50° C. overnight. 0.230 g of a yellow solid is obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. addition50 ml of a saturated solution of sodium hydrogen carbonate are added to the residue
  3. customThe precipitate obtained
  4. filtrationis filtered off
  5. customdried under reduced pressure at 50° C. overnight

Sources & evidence

ORD record
ord-4ffe1302db8d4c0ab8042a09e0834f1f
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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