Acetonitrile → 5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-amine

HRID 84127Notes

Reaction equation

HRID 84127 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[N:23]=[N:24][N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:26]=2)=[N:20][C:19]([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH:42]([CH3:44])[CH3:43])(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CC#N>C(Cl)Cl>[CH:42]([S:39]([C:36]1[CH:35]=[CH:34][C:33]([C:19]2[N:20]=[C:21]([C:22]3[N:23]=[N:24][N:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:26]=3)[C:16]([NH2:8])=[N:17][CH:18]=2)=[CH:38][CH:37]=1)(=[O:41])=[O:40])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 86682767tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(1-phenyltriazol-4-yl)pyrazin-2-yl]carbamate

Product 1

HCID 715219715-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(1-phenyltriazol-4-yl)pyrazin-2-yl]carbamate (193 mg, 0.3109 mmol) in DCM (3 mL) was added TFA (1 mL). The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was concentrated in vacuo, more DCM was added and concentrated in vacuo to leave a yellow solid. The solid was sonicated in a small amount of MeCN and solid collected by filtration and dried by suction to provide the sub-titled product 5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-amine Compound I-1 as a pale yellow solid (105 mg, 80%). 1H NMR (400.0 MHz, DMSO-d6) δ 9.66 (s, 1H), 8.85 (s, 1H), 8.46 (d, 2H), 8.12 (d, 2H), 7.91 (d, 2H), 7.74 (br s, 2H), 7.67 (t, 2H), 7.58 (t, 1H), 3.47 (quintet, 1H) and 1.19 (d, 6H) ppm; LC/MS m/z 421.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, more DCM
  2. additionwas added
  3. concentrationconcentrated in vacuo
  4. customto leave a yellow solid
  5. filtrationcollected by filtration
  6. customdried by suction

Sources & evidence

ORD record
ord-f388dc5c6fe5417998ccb9cd781054cf
Source dataset
uspto-grants-2014_09
Patent number
US08846917B2

Reaction notes

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