Pyridine → HCID 57663212, compound

HRID 548741Notes

Reaction equation

HRID 548741 reaction equation
[Cl:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][C@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[CH:24]=1)[C:19](O)=[O:20].N1C=CC=CC=1.[NH2:37][C:38]1[CH:42]=[CH:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[N:39]=1>C(Cl)Cl>[Cl:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([C:19]([NH:37][C:38]2[CH:42]=[CH:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[N:39]=2)=[O:20])[CH:22]=[C:23]([O:25][C@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 51358380tert-Butyl 3-amino-1H-pyrazole-1-carboxylateHCID 57663190HCID 57663190, compound

Product 1

HCID 57663212HCID 57663212, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-N,N-2-trimethylpropenylamine (0.09 mL, 0.37 mmol) was added to a solution of 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid (145 mg, 0.34 mmol) in DCM (5 mL) and the reaction stirred at RT for 30-40 minutes. Pyridine (0.055 mL, 0.67 mmol) and 1,1-dimethylethyl 3-amino-1H-pyrazole-1-carboxylate (123 mg, 0.67 mmol) were added and the reaction stirred for 2 hours at RT. The reaction mixture was evaporated in vacuo and water (20 mL) added. The mixture was extracted with ethyl acetate (3×20 mL), washed with 1N hydrochloric acid (20 mL), a saturated solution of sodium hydrogen carbonate (20 mL), brine (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0-5% methanol in DCM, to give the desired compound as a pale yellow oil (107 mg). m/z 611 (M−H)−

Workup

  1. stirringthe reaction stirred for 2 hours at RT
  2. customThe reaction mixture was evaporated in vacuo and water (20 mL)
  3. additionadded
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. washwashed with 1N hydrochloric acid (20 mL)
  6. dry with materiala saturated solution of sodium hydrogen carbonate (20 mL), brine (20 mL), dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe crude product was chromatographed on silica
  9. washeluting with a gradient of 0-5% methanol in DCM

Sources & evidence

ORD record
ord-e98d7e2f70794db78a9edc08ea72fcb2
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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