Methylhydrazine → 4-(Cyclopentylamino)-1-ethyl-N-[methyl]-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490876ノート

反応式

HRID 490876 の反応式
[CH:1]1([NH:6][C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(O[N:29]1[N:37]=NC2C=CC=C[C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CNN>CN(C=O)C.C(Cl)CCl>[CH:1]1([NH:6][C:7]2[C:12]([C:13]([N:29]([CH3:30])[NH2:37])=[O:15])=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

8

反応物 5

HCID 6061MethylhydrazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576751554-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid2 回

生成物 1

HCID 576751694-(Cyclopentylamino)-1-ethyl-N-[methyl]-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Intermediate 3 (0.10 g) was dissolved in DMF (2 ml) and treated with HBTU (0.136 g) and DIPEA (0.116 g). A separate portion of Intermediate 3 (0.10 g) was dissolved in DMF (2 ml) and treated with EDC (0.096 g) and HOBT (0.058 g). The resultant suspensions were both stirred under nitrogen for 15 min, then methyl hydrazine (0.017 g) added to each and stirring continued under nitrogen for 18 h. The mixtures were independently concentrated in vacuo and the residues partitioned between DCM and water. The organic layers were concentrated and each applied to an SPE cartridge (aminopropyl, 2 g) which was eluted with methanol, followed by 10% ammonia in methanol. The two portions of Intermediate 7 thus afforded were combined (0.16 g). LCMS showed MH+=303; TRET=2.22 min.

後処理

  1. stirringstirring
  2. waitcontinued under nitrogen for 18 h
  3. concentrationThe mixtures were independently concentrated in vacuo
  4. customthe residues partitioned between DCM and water
  5. concentrationThe organic layers were concentrated
  6. washwas eluted with methanol

出典と根拠

ORDレコード
ord-a396932381784cdaa7c001dcef5ed58b
出典データセット
uspto-grants-2009_05
特許番号
US07528148B2

反応ノート

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