Ammonium Chloride → HCID 67205335, compound

HRID 387777Notes

Reaction equation

HRID 387777 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26]O[CH2:24][CH2:23]1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:57])[NH:37][C:38]2[CH:56]=[CH:55][C:41]([O:42][C:43]3[C:44]4[CH:51]=[C:50]([C:52](O)=[O:53])[NH:49][C:45]=4[N:46]=[CH:47][N:48]=3)=[CH:40][CH:39]=2)=[CH:31][CH:30]=1.[Cl-].[NH4+]>C(N(CC)CC)C.CN(C)C=O>[CH2:27]([N:22]([CH2:23][CH3:24])[CH2:21][CH2:20][CH2:19][NH:18][C:52]([C:50]1[NH:49][C:45]2[N:46]=[CH:47][N:48]=[C:43]([O:42][C:41]3[CH:55]=[CH:56][C:38]([NH:37][C:36]([NH:35][C:32]4[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=4)=[O:57])=[CH:39][CH:40]=3)[C:44]=2[CH:51]=1)=[O:53])[CH3:26]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 61055N-(3-Aminopropyl)morpholineHCID 199401P,P-Diphenylphosphinic azideHCID 58931116HCID 58931116, compound

Product 1

HCID 67205335HCID 67205335, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

After adding 0.8 ml of dimethylformamide, 21 μl of triethylamine, 9.5 μl of diphenylphosphoryl azide (DPPA) and 6.5 μl of 4-(3-aminopropyl)morpholine to 12 mg of the 4-{4-[3-(4-fluorophenyl)ureido]phenoxy)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid synthesized in Production Example 164, the mixture was stirred at room temperature for 2 days. Saturated ammonium chloride was added, liquid separation and extraction were performed with an ethyl acetate-tetrahydrofuran mixed solvent, and the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered with plug cotton and concentrated to dryness to obtain 9 mg of the title compound.

Workup

  1. customsynthesized in Production Example 164
  2. customliquid separation and extraction
  3. washthe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered with plug cotton
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2be25f603db8487aaccb7d87e4a1010c
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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