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 446913노트

반응식

HRID 446913 반응식
[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

참가 물질

6

반응물 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

생성물 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-carboxamide수율 118.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c983d4e1608481a801ea5afc3134ffa
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481538B2

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