Sodium Hydroxide → HCID 118159555, compound

HRID 628390Notes

Reaction equation

HRID 628390 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([CH:35]=O)[CH:34]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:15]([CH3:18])=[N:16][N:17]=3)[C:9]=2[CH:8]=[C:7]1[C:19]([O:21]CC1C=C(C=O)C=C(Cl)C=1)=[O:20].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([CH2:35][N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:34]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:15]([CH3:18])=[N:16][N:17]=3)[C:9]=2[CH:8]=[C:7]1[C:19]([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 118159777HCID 118159777, compound

Product 1

HCID 118159555HCID 118159555, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-5-formylbenzyl 6-(3-chloro-5-formylbenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (0.035 g, 0.067 mmol, from Example 131, Step 7) was suspended in DCM (4 mL) and pyrrolidine (0.03 g, 0.4 mmol, Aldrich) and sodium triacetoxyborohydride (0.2 g, 0.8 mmol, Aldrich) were added. After stirring overnight, the reaction mixture was made basic by the addition of 1N solution of NaOH, and the product was extracted with EtOAc. The organic extract was dried over sodium sulfate, filtered and concentrated. The crude product was stirred with 1.0 M solution of NaOH (2 mL, 2 mmol) and THF (2 mL) for 1.5 hours. The product was purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (5 mg, 18%). LCMS (M+H)+: 424.2.

Workup

  1. extractionthe product was extracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by preparative HPLC-MS (Waters XBridge C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-e7e3c9b00fd14e4aa339aad01fe7f2c0
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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