Ethanol → HCID 59471618, compound

HRID 78648Notes

Reaction equation

HRID 78648 reaction equation
[CH3:1][NH2:2].C(O)C.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][C:17]([C:19]3[C:20]([NH2:37])=[N:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([S:31]([CH:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])=[CH:27][CH:26]=4)[N:24]=3)=[N:16][N:15]=2)=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[CH:34]([S:31]([C:28]1[CH:29]=[CH:30][C:25]([C:23]2[N:24]=[C:19]([C:17]3[O:18][C:14]([C:11]4[CH:10]=[CH:9][C:8]([CH2:7][NH:2][CH3:1])=[CH:13][CH:12]=4)=[N:15][N:16]=3)[C:20]([NH2:37])=[N:21][CH:22]=2)=[CH:26][CH:27]=1)(=[O:33])=[O:32])([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 59472016HCID 59472016, compound

Product 1

HCID 59471618HCID 59471618, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

MeNH2 in ethanol (184.9 g, 243.6 mL of 33% w/w, 1.965 mol) was added in one portion to a stirred solution of 3-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (10.11 g, 19.65 mmol) in CH2Cl2 (1.01 L) and methanol (1.01 L) and the resulting mixture stirred overnight at room temperature. Nitrogen was bubbled through reaction for 2 h and then the reaction mixture was concentrated in vacuo. The crude material was stirred in K2CO3 (393.0 mL of 0.25 M, 98.25 mmol) for 2 h and then isolated by filtration and washed with water. Triturated with warm acetonitrile to leave the product as a yellow solid (7.19 g, 75% yield); 1H NMR (400 MHz, DMSO) d 1.19-1.21 (d, 6H), 2.30 (m, 3H), 3.35-3.49 (m, 1H), 3.77 (m, 2H), 7.61-7.63 (d, 2H), 7.97-7.99 (d, 2H), 8.11-8.13 (d, 2H), 8.39-8.41 (d, 2H) and 9.06 (s, 1H) ppm; MS (ES+) 465.4

Workup

  1. customNitrogen was bubbled through reaction for 2 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customisolated by filtration
  4. washwashed with water
  5. customTriturated with warm acetonitrile

Sources & evidence

ORD record
ord-5d0b97a4b98340a5b29bdecfef69a9b6
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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