Ammonium Chloride → HCID 56597372, compound

HRID 409541Notes

Reaction equation

HRID 409541 reaction equation
[Cl-].[NH4+].C([N:6](CC)C(C)C)(C)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[O: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](O)=[O:64])[N:52]=3)=[O:50])[CH:41]=2)[NH:36]1.C(=O)([O-])O.[Na+]>CN(C=O)C>[O: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]([NH2:6])=[O:64])[N:52]=3)=[O:50])[CH:41]=2)[NH:36]1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 56597371HCID 56597371, compound

Product 1

HCID 56597372HCID 56597372, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.7 mg (0.2 mmol) of ammonium chloride, 5.17 mg (0.4 mmol) of N,N-diisopropylethylamine and 49.2 mg (0.2 mmol) of TOTU are added, at 0° C., under an inert atmosphere, to 46.8 mg (0.1 mmol) of 3-{3-[(2,4-dioxo-3-propyl-1,2,3,4-tetrahydroquinazolin-6-yl)carbonyl]imidazo[1,5-a]pyridin-1-yl}benzoic acid in 2 ml of DMF. The reaction medium is stirred for 12 hours at ambient temperature and then poured into 30 ml of a saturated solution of sodium hydrogen carbonate. The precipitate obtained is filtered off, washed with water, and dried under reduced pressure at 40° C. overnight. 0.042 g of a yellow solid is obtained.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-2a2d681e4a274a3c86451b45eb92f2db
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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