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1,2-Dichloroethane → HCID 56599078, compound

HRID 476076
Notes
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Reaction equation

HRID 476076 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:21](O)=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:24][CH2:25][C:26]1[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=1[CH3:32].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:21]([NH:24][CH2:25][C:26]3[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]4)[C:8]=3[N:9]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 67124533HCID 67124533, compound

Product 1

HCID 56599078HCID 56599078, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Cyclopropyl-3-methyl-1-(1-methyl-4-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.477 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (117 mg, 0.620 mmol), 1-hydroxy-7-azabenzotriazole (130 mg, 0.954 mmol), EDC (183 mg, 0.954 mmol) and N-methylmorpholine (0.210 mL, 1.909 mmol) were suspended in DMSO (10 mL) and stirred at room temperature for 16 h. Next was added 25 mL of water, stirred for 10 minutes, and then extracted with EtOAc (5×). The organic layers were concentrated in vacuo to afford 20 mg product. The aqueous phase was concentrated in vacuo and the crude residue purified by reverse phase HPLC (mobile phase: 10-60% ACN in H2O, 0.1% NH4OH) to afford additional product. The final product was collected as a solid, 0.100 g (47%). LCMS E-S (M+H)=449.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.05 (m, 4H), 1.79 (d, J=9.60 Hz, 2H), 2.11 (s, 3H), 2.15 (d, J=8.34 Hz, 3H), 2.21 (s, 3H), 2.23-2.27 (m, 3H), 2.35 (s, 3H), 2.91 (d, J=8.08 Hz, 2H), 4.33 (d, J=4.80 Hz, 2H), 4.49-4.72 (m, 1H), 5.86 (s, 1H), 6.97 (s, 1H), 6.92-7.07 (m, 1H), 8.58 (t, J=4.93 Hz, 1H), 11.50 (s, 1H).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with EtOAc (5×)
  3. concentrationThe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-522ca7877db74b159128e6615d5ca3b9
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637509B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes