1,2-Dichloroethane → HCID 68082872, compound

HRID 476121Notes

Reaction equation

HRID 476121 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13](O)=[O:14])[C:7]=2[C:6]([N+]([O-])=O)=[N:5]1)[CH3:3].Cl.[NH2:26][CH2:27][C:28]1[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34].C1C=NC2[N:43]([OH:46])N=NC=2C=1.C(Cl)CCl.CN1CC[O:55]CC1.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.O>[CH3:34][C:33]1[CH:32]=[C:31]([CH3:35])[NH:30][C:29](=[O:36])[C:28]=1[CH2:27][NH:26][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:8]=2[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:43]([O-:46])=[O:55])[CH:11]=1)=[O:14]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 10340Sodium CarbonateHCID 181649HOAtHCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideHCID 67124242HCID 67124242, compound

Product 1

HCID 68082872HCID 68082872, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

1-(1-Methylethyl)-3-nitro-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (24 mg, 0.074 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (18 mg, 0.096 mmol), HOAT (17 mg, 0.110 mmol) and EDC (21 mg, 0.110 mmol) were suspended in DMSO (800 μL) and the reaction mixture stirred at room temperature. Next added 4-methylmorpholine (41 μl, 0.368 mmol), and the reaction was stirred at room temperature for 16 h. The reaction mixture was added dropwise to cold, slightly basic solution of water (3 mL) and 1N Na2CO3 (0.5 mL). After stirring for 20 min., the precipitated solids were collected via vacuum filtration and washed with water. The solid was dried on the high vacuum (72 h). The product, was collected as an off-white powder (28 mg, 82%). LCMS E-S (M+H)=461.1. 1H NMR (400 MHz, DMSO-d6) δ 9.01 (br. s., 1H), 8.42 (s, 1H), 8.02 (ddd, J=1.14, 4.99, 7.77 Hz, 2H), 7.99 (s, 1H), 7.86 (td, J=1.26, 7.58 Hz, 1H), 7.72-7.77 (m, 1H), 5.90 (s, 1H), 5.04 (quin, J=6.69 Hz, 1H), 4.41 (d, J=4.55 Hz, 1H), 3.34 (s, 2H), 2.22 (s, 3H), 2.12 (s, 3H), 1.49 (d, J=6.57 Hz, 6H).

Workup

  1. stirringthe reaction was stirred at room temperature for 16 h
  2. stirringAfter stirring for 20 min.
  3. filtrationthe precipitated solids were collected via vacuum filtration
  4. washwashed with water
  5. customThe solid was dried on the high vacuum (72 h)
  6. customThe product, was collected as an off-white powder (28 mg, 82%)

Sources & evidence

ORD record
ord-660f144746fa4e75a86f70ab03aabefb
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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