Ammonia → HCID 86689730, compound

HRID 1396367Notes

Reaction equation

HRID 1396367 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([Cl:23])=[CH:10][C:11]=1[NH:12][C:13]1[N:18]=[C:17]2[N:19]([CH3:22])[CH:20]=[CH:21][C:16]2=[CH:15][CH:14]=1)=O)C.[NH3:24]>CO>[Cl:23][C:9]1[N:8]=[N:7][C:6]([C:4]([NH2:24])=[O:3])=[C:11]([NH:12][C:13]2[N:18]=[C:17]3[N:19]([CH3:22])[CH:20]=[CH:21][C:16]3=[CH:15][CH:14]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866897296-chloro-4-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 86689730HCID 86689730, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-4-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-pyridazine-3-carboxylic acid ethyl ester (52 mg, 0.157 mmol) was suspended in 7M ammonia in methanol (2 mL). After 2 h, the reaction mixture was concentrated in vacuo to give 6-chloro-4-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-pyridazine-3-carboxylic acid amide (47 mg, 100%) as a light yellow solid which was used directly in the next step without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.07 (s, 1H) 9.24 (s, 1H) 8.85 (br. s., 1H) 8.21 (br. s., 1H) 7.99 (d, J=8.3 Hz, 1H) 7.42 (d, J=3.3 Hz, 1H) 6.81 (d, J=8.3 Hz, 1H) 6.45 (d, J=3.3 Hz, 1H) 3.83 (s, 3H); LCMS (EI/CI) m/z: 303 [M+H].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-33bfb33d4aa24f019df4b9c23b6bb844
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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