Acetic Acid → HCID 67995088, compound

HRID 2361377Notes

Reaction equation

HRID 2361377 reaction equation
[NH2:1][C:2]1[C:3]([CH3:30])=[C:4]([C:8]2[C:20]3[C:19]4[CH:18]=[CH:17][C:16]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:15][C:14]=4[NH:13][C:12]=3[C:11]([C:26]([O:28][CH3:29])=[O:27])=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([CH:41]=O)=[C:36]([CH:40]=1)[C:37]([OH:39])=[O:38].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O1CCCC1.CCOC(C)=O.O>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:41][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[C:20]4[C:19]5[CH:18]=[CH:17][C:16]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:15][C:14]=5[NH:13][C:12]=4[C:11]([C:26]([O:28][CH3:29])=[O:27])=[N:10][N:9]=3)[C:3]=2[CH3:30])=[C:36]([CH:40]=1)[C:37]([OH:39])=[O:38]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride2×HCID 71762095-Chloro-2-formylbenzoic acidHCID 67994675HCID 67994675, compound

Product 1

HCID 67995088HCID 67995088, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a homogeneous, burgundy solution of methyl 1-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-5H-pyridazino[4,5-b]indole-4-carboxylate (0.1603 g, 0.394 mmol), 5-chloro-2-formylbenzoic acid (0.182 g, 0.986 mmol) and acetic acid (0.056 mL, 0.986 mmol) in dichloromethane (7.89 mL) and tetrahydrofuran (5.26 mL) under nitrogen was added sodium triacetoxyborohydride (0.251 g, 1.183 mmol), and the reaction was stirred overnight. More sodium triacetoxyborohydride (146.2 mg) was added. After 1 hr, water (6 mL) was added, and the reaction was stirred for 30 min. It was dissolved in EtOAc (100 mL) and washed with water (3×30 mL) and brine (30 mL), dried over MgSO4, and concentrated in vacuo to give a crude product, which was used in the subsequent step.

Workup

  1. waitAfter 1 hr
  2. stirringthe reaction was stirred for 30 min
  3. washwashed with water (3×30 mL) and brine (30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e9d48753264e879b01e2042600fa04
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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