Ammonium Chloride → HCID 57526815, compound

HRID 1452620Notes

Reaction equation

HRID 1452620 reaction equation
[C:1]([O:5][C:6]([N:8]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH2:50][O:51][CH3:52])=[CH:44][CH:43]=1)[C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)[C:10]=1[CH2:32][CH2:33][O:34][Si](C(C)(C)C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:42]1[CH:43]=[CH:44][C:45]([O:48][CH2:49][CH2:50][O:51][CH3:52])=[CH:46][CH:47]=1)[C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:20]2)[C:10]=1[CH2:32][CH2:33][OH:34])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57526820HCID 57526820, compound

Product 1

HCID 57526815HCID 57526815, compoundYield 142.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (5 mL) solution containing tert-butyl (S)-3-{7-{tert-butoxycarbonyl-[4-(2-methoxyethoxy)phenyl]amino}-6-[2-(tert-butyldimethylsilanyloxy)ethyl]pyrazolo[1,5-a]pyrimidin-5-ylamino}piperidine-1-carboxylate (193 mg, 0.261 mmol), tetrabutylammonium fluoride (474 μL, 0.474 mmol) was added, and this mixture was stirred at room temperature for 1.5 hr. After the reaction, aqueous ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated to obtain the title compound (233 mg).

Workup

  1. additionwas added
  2. additionwas added to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ce2ead4f67c84482ba39a08df1b3dcfb
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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