Ammonium Chloride → HCID 71746494, compound

HRID 518891Notes

Reaction equation

HRID 518891 reaction equation
C([N:4](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].[CH3:36][N:37]1[CH2:42][CH2:41][CH:40]([C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50]3[N:51]=[CH:52][C:53]4[S:58][C:57]([C:59]([OH:61])=O)=[C:56]([C:62]5[CH:63]=[N:64][NH:65][CH:66]=5)[C:54]=4[N:55]=3)=[C:45]([O:67][CH:68]([CH3:70])[CH3:69])[CH:44]=2)[CH2:39][CH2:38]1>CN(C)C=O.CO>[CH3:36][N:37]1[CH2:38][CH2:39][CH:40]([C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50]3[N:51]=[CH:52][C:53]4[S:58][C:57]([C:59]([NH2:4])=[O:61])=[C:56]([C:62]5[CH:66]=[N:65][NH:64][CH:63]=5)[C:54]=4[N:55]=3)=[C:45]([O:67][CH:68]([CH3:70])[CH3:69])[CH:44]=2)[CH2:41][CH2:42]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86698042HCID 86698042, compound

Product 1

HCID 71746494HCID 71746494, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

123 mg of N,N-diisopropylethylamine, 181 mg of HATU and 14 mg of ammonium chloride are added to a solution of 117 mg of 2-{[4-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]amino}-7-(1H-pyrazol-4-yl)thieno[3,2-d]pyrimidine-6-carboxylic acid in 6 ml of dimethylformamide. The reaction medium is stirred for 16 hours at ambient temperature and then concentrated to dryness under reduced pressure. Purification is carried out by flash chromatography on alumina, elution being carried out with a mixture of dichloromethane and methanol (+10% NH4OH) (95/5). The product resulting from the column purification is taken up in methanol and is purified by preparative thin layer chromatography (eluent: dichloromethane/methanol (+10% NH4OH) (95/5)), so as to give 23 mg of 2-{[4-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]amino}-7-(1H-pyrazol-4-yl)thieno[3,2-d]pyrimidine-6-carboxamide in the form of a yellow solid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customPurification
  3. washis carried out by flash chromatography on alumina, elution
  4. additionbeing carried out with a mixture of dichloromethane and methanol (+10% NH4OH) (95/5)
  5. customThe product resulting from the column purification
  6. customis purified by preparative thin layer chromatography (eluent: dichloromethane/methanol (+10% NH4OH) (95/5))

Sources & evidence

ORD record
ord-140bad02951143a0a5f8cd233b793598
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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