1,2-Dichloroethane → N'-acetyl-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide

HRID 588141Notes

Reaction equation

HRID 588141 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](O)=[O:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[C:35]([NH:38][NH2:39])(=[O:37])[CH3:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:35]([NH:38][NH:39][C:8]([C:6]1[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:4]=2[CH:3]=[C:2]([Cl:1])[N:7]=1)=[O:9])(=[O:37])[CH3:36]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 14039AcetohydrazideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1182718276-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid

Product 1

HCID 118271701N'-acetyl-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid (36B, 96 mg, 0.204 mmol), acethydrazide (22.70 mg, 0.306 mmol), EDC (58.7 mg, 0.306 mmol), and HOBT (46.9 mg, 0.306 mmol) were taken up in DMF (2043 μl). DIPEA (143 μl, 0.817 mmol) was added and the reaction mixture was allowed to stir at rt overnight. The reaction was heated to 60 C for 1 hour. Saturated NH4Cl and EtOAc were added. The products were extracted into EtOAc (2×). The combined organics were then washed with saturated NaHCO3 and brine, then dried over MgSO4, and concentrated in vacuo to give N′-acetyl-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide. MS: [M+H]+ m/z 526.

Workup

  1. temperatureThe reaction was heated to 60 C for 1 hour
  2. extractionThe products were extracted into EtOAc (2×)
  3. washThe combined organics were then washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36fe42b4dc5b4a0290bd770e02ba18b8
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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