Diisopropylethylamine → N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}pentanediamide

HRID 657385ノート

反応式

HRID 657385 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[F:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:43][CH2:44][C:45]1[C:50]([CH2:51][CH3:52])=[N:49][C:48]2[N:53]([CH2:56][CH3:57])[N:54]=[CH:55][C:47]=2[C:46]=1[NH:58][CH:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([NH:43][CH2:44][C:45]2[C:46]([NH:58][CH:59]3[CH2:60][CH2:61][O:62][CH2:63][CH2:64]3)=[C:47]3[CH:55]=[N:54][N:53]([CH2:56][CH3:57])[C:48]3=[N:49][C:50]=2[CH2:51][CH3:52])=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578198715-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic AcidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

生成物 1

HCID 57819876N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}pentanediamide収率 112.5%

試薬・触媒・溶媒 1

HCID 21919333Tetrahydrofurane dichloromethane溶媒

実験手順

A mixture of 5-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic acid (920 mg, 2.89 mmol), HBTU (1130 mg, 2.98 mmol), 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (820 mg, 2.71 mmol) and diisopropyl ethyl amine (1 mL) in DCM/THF (1:1, 100 mL) was stirred at room temperature overnight. The mixture was concentrated, mixed with EtOAc (50 mL) and washed by NaHCO3 (50 mL) and NH4Cl (50 mL). The organic parts were collected, dried and concentrated to afford the desired product (1.84 g).

後処理

  1. concentrationThe mixture was concentrated
  2. additionmixed with EtOAc (50 mL)
  3. washwashed by NaHCO3 (50 mL) and NH4Cl (50 mL)
  4. customThe organic parts were collected
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-707727b27b7e444090057df593cd72cc
出典データセット
uspto-grants-2011_12
特許番号
US08071588B2

反応ノート

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