Ammonium Chloride → HCID 66590062, compound

HRID 1092059Notes

Reaction equation

HRID 1092059 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.[NH2:28][C:29]1[N:33](C(OC(C)(C)C)=O)[N:32]=[C:31]([CH2:41][CH2:42][C:43]2[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[C:45]([O:51][CH3:52])[CH:44]=2)[CH:30]=1.[NH4+].[Cl-]>C1COCC1>[CH3:50][O:49][C:47]1[CH:48]=[C:43]([CH2:42][CH2:41][C:31]2[NH:32][N:33]=[C:29]([NH:28][C:22](=[O:24])[C:21]3[CH:20]=[CH:19][C:18]([CH:15]4[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]4)=[CH:27][CH:26]=3)[CH:30]=2)[CH:44]=[C:45]([O:51][CH3:52])[CH:46]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 49760144Methyl 4-(1-methylpiperidin-4-YL)benzoateHCID 57440371Tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate

Product 1

HCID 66590062HCID 66590062, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of NaHMDS (1M in THF) (5.91 mL, 5.91 mmol) was added dropwise to a stirred solution of methyl 4-(1-methylpiperidin-4-yl)benzoate (0.4594 g, 1.97 mmol) and tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]-1H-pyrazole-1-carboxylate (0.821 g, 2.36 mmol) in THF (4 mL), over a period of 10 mins under nitrogen. The resulting solution was stirred at room temperature for 18 h. The reaction mixture was poured into saturated NH4Cl (25 mL), extracted with EtOAc (2×25 mL), washed with saturated brine and dried over MgSO4, filtered and evaporated to afford the crude product (1.0719 g) as an orange gum. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.142 g, 16.08%) as a white solid;

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washwashed with saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude product (1.0719 g) as an orange gum
  7. customThe crude product was purified by preparative HPLC
  8. additionFractions containing the desired compound
  9. customwere evaporated to dryness

Sources & evidence

ORD record
ord-8ac2707f45a043e792ad9705601ca1b6
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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