Acetic Acid → HCID 59577330, compound

HRID 1773390Notes

Reaction equation

HRID 1773390 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([F:30])[CH:29]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:26])[C:17]1[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:18]=1[F:25].[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[OH-]>C1COCC1.O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([F:30])[CH:29]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:26])[C:17]1[CH:22]=[C:21]([CH2:23][N:35]2[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]2)[CH:20]=[CH:19][C:18]=1[F:25]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86647621HCID 86647621, compound

Product 1

HCID 59577330HCID 59577330, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[5-(3,5-Difluoro-benzyl)-1H-indazol-3-yl]-2-fluoro-5-formyl-benzamide (150 mg, 0.367 mmol) in THF (4 mL), under a nitrogen atmosphere, at room temperature was treated with N-methylpiperazine ((0.039 mL, 0.367 mmol) and then with acetic acid (0.024 mL, 0.422 mmol). After 0.5 hours sodium triacetoxyborohydride was added and the reaction was stirred over night. EtOAc (25 mL) and water (25 mL) were added, pH was adjusted to 11 with concentrated NH4OH. The organic layer was separated and the aqueous layer was extracted twice with EtOAc (2×10 mL). The combines organic extracts were dried over sodium sulphate, evaporated to dryness and purified over silica gel (Eluent:DCM: 7N NH3 in MeOH 96:4) affording 177 mg of title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with EtOAc (2×10 mL)
  3. dry with materialThe combines organic extracts were dried over sodium sulphate
  4. customevaporated to dryness
  5. custompurified over silica gel (Eluent:DCM: 7N NH3 in MeOH 96:4)

Sources & evidence

ORD record
ord-02f41f2d9087480bb67f051adf03a949
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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