Dimethylformamide → Cyclopentanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide

HRID 449030Notes

Reaction equation

HRID 449030 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([NH2:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=[O:58])C>>[Cl:1][C:2]1[C:3]([CH:8]([NH:22][C:41]([CH:46]2[CH2:42][CH2:43][CH2:44][CH2:45]2)=[O:58])[C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59341168HCID 59341168, compound

Product 1

HCID 86636031Cyclopentanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amideYield 81.7%

Procedure

In a 10 mL flask were added C-(3-chloropyrazin-2-yl)-C-(4-phenoxyphenyl)-methylamine (75 mg, 0.24 mmol), DIEA (0.38 mL, 0.0022 mol), TBTU (0.12 g, 0.00036 mol) and DMF (4 mL, 0.05 mol) and the reaction mixture is stirred at rt overnight. Reaction mixture was concentrated in vacuo and washed with sat NaHCO3, brine extracting with DCM. The organic layer was concentrated to give a dark yellow solid. Purification by prep TLC using 50% EtOAc: hexanes afforded 80 mg of the title compound as an off white solid. MS (ES+): m/z 407.86 (50)[MH+]. HPLC: tR=3.75 min (Open Lynx, polar—5 min).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. washwashed
  4. concentrationThe organic layer was concentrated
  5. customto give a dark yellow solid
  6. customPurification by prep TLC

Sources & evidence

ORD record
ord-19150e23b9364cc9a3d23c0162dc9e83
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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