Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]thieno[3,2-b]pyridine-2-carboxamide

HRID 658181ノート

反応式

HRID 658181 の反応式
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CN(C(ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:37](N(CC)C(C)C)(C)[CH3:38]>CN(C=O)C>[N:27]12[CH2:26][CH2:25][CH:24]([CH2:37][CH2:38]1)[C@@H:23]([NH:28][C:10]([C:2]1[S:1][C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=1)=[O:12])[CH2:22]2

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22047169Thieno[3,2-b]pyridine-2-carboxylic acid

生成物 1

HCID 10125449N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]thieno[3,2-b]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

35 mg (0.20 mmol) of thieno[3,2-b]pyridine-2-carboxylic acid, 58.3 mg (0.29 mmol) of R-3-aminoquinuclidine dihydrochloride, 111.4 mg (0.29 mmol) of HATU, 138.8 mg (1.07 mmol) of N,N-diisopropylethylamine and 1.5 ml of DMF are reacted according to the general procedure (variant A). The reaction mixture is purified by preparative HPLC and then subjected to fine purification on silica gel 60 (mobile phase: dichloromethane/methanol/ammonia 90:9:1). 44 mg (78% of theory) of the title compound are isolated.

後処理

  1. customThe reaction mixture is purified by preparative HPLC
  2. customsubjected to fine purification on silica gel 60 (mobile phase: dichloromethane/methanol/ammonia 90:9:1)

出典と根拠

ORDレコード
ord-1544df56cb9547588d2f2025cb2ddd18
出典データセット
uspto-grants-2011_12
特許番号
US08076355B2

反応ノート

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