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 446913ノート

反応式

HRID 446913 の反応式
[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

参加物

6

反応物 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

生成物 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-carboxamide収率 118.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-0c983d4e1608481a801ea5afc3134ffa
出典データセット
uspto-grants-2013_07
特許番号
US08481538B2

反応ノート

読み込み中…