Acetic Acid → HCID 67994837, compound

HRID 2361389Notes

Reaction equation

HRID 2361389 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:18]=4[CH3:24])=[N:15][N:14]=[C:13]([C:25]([NH2:27])=[O:26])[C:9]=3[NH:10][C:11]=2[CH:12]=1)(=[O:3])[CH3:2].[CH:28]([C:30]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:31]=1[C:32]([OH:34])=O)=[O:29].C(O[BH-](OC(=O)C)OC(=O)C)(=[O:43])C.[Na+].C(O)(=O)C>ClCCl.O1CCCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:16]([C:17]4[C:18]([CH3:24])=[C:19]([NH:23][C:32]([C:31]5[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:30]=5[C:28]([OH:29])=[O:43])=[O:34])[CH:20]=[CH:21][CH:22]=4)=[N:15][N:14]=[C:13]([C:25](=[O:26])[NH2:27])[C:9]=3[NH:10][C:11]=2[CH:12]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride3×HCID 71762052-Formyl-5-methoxybenzoic acidHCID 67994528HCID 67994528, compound

Product 1

HCID 67994837HCID 67994837, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-acetyl-1-(3-amino-2-methylphenyl)-5H-pyridazino[4,5-b]indole-4-carboxamide (0.250 g, crude product from the previous step), 2-formyl-5-methoxybenzoic acid (0.251 g, 1.391 mmol), sodium triacetoxyborohydride (0.442 g, 2.087 mmol), and acetic acid (0.100 mL, 1.739 mmol) in dichloromethane (18 mL) and tetrahydrofuran (18 mL) was stirred at room temperature for 3 hr. Additional sodium triacetoxyborohydride (0.442 g, 2.087 mmol) was added and the reaction mixture was stirred at rt. Three hours later, another portion of sodium triacetoxyborohydride (0.442 g, 2.087 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction was quenched with water (30 mL) and the mixture was extracted with ethyl acetate (4×40 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the crude desired product (0.336 g) as a beige solid.

Workup

  1. stirringthe reaction mixture was stirred at rt
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe reaction was quenched with water (30 mL)
  4. extractionthe mixture was extracted with ethyl acetate (4×40 mL)
  5. extractionThe combined extract
  6. dry with materialwas dried over anhydrous MgSO4
  7. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-a5196cdb585a4dcaac5c3f1a10411c5b
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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