Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol 6-(furan-3-yl)pyrazine-2-carboxamide

HRID 446913Notes

Reaction equation

HRID 446913 reaction equation
[NH2:1][C@@H](C1[N:11]2[C:7]([S:8][C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)=[N:10]2)=NN=1)C.[NH2:20][C:21]1[C:22]([C:32]([OH:34])=O)=[N:23][C:24]([C:27]2[CH:31]=[CH:30][O:29][CH:28]=2)=[CH:25][N:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH2:23][CH:22]([C:21]1[N:10]2[C@H:9]([S:8][CH:7]=[N:11]2)[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[N:20]=1)[CH3:32].[O:29]1[CH:30]=[CH:31][C:27]([C:24]2[N:23]=[C:22]([C:32]([NH2:1])=[O:34])[CH:21]=[N:26][CH:25]=2)=[CH:28]1

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59363289(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amineHCID 593633043-Amino-6-(furan-3-yl)pyrazine-2-carboxylic acid

Product 1

HCID 68705325(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol 6-(furan-3-yl)pyrazine-2-carboxamideYield 118.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(Step 8-v) To a mixture of (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine (0.141 g, 0.483 mmol) in DMF (3 mL) was added 3-amino-6-(furan-3-yl)pyrazine-2-carboxylic acid (0.066 g, 0.322 mmol), HBTU (0.159 g, 0.42 mmol), and TEA (0.135 ml, 0.966 mmol). After two hours the mixture was diluted with water and the resulting solids were collected. The solids were washed sequentially with 20% ethanol/ethyl ether, methylene chloride, and methanol, then dried in vacuo to provide (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-(furan-3-yl)pyrazine-2-carboxamide (0.09 g): 1H NMR 300 MHz DMSO-d6 10.8 (s, 1H), 9.21 (s, 1H), 8.61 (s, 1H), 8.38 (s, 1H), 7.68 (s, 1H), 7.51 (s, 1H), 7.39 (d, 2H), 7.13 (m, 3H), 7.05 (d, 2H), 5.69 (m, 1H), 1.76 (d, 3H); ESMS MH+=482.

Workup

  1. customthe resulting solids were collected
  2. washThe solids were washed sequentially with 20% ethanol/ethyl ether, methylene chloride, and methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0c983d4e1608481a801ea5afc3134ffa
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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