3-Methoxypropylamine → [5-({[3-(Methyloxy)propyl]amino}methyl)-2-thienyl]boronic acid

HRID 562184

反応式

HRID 562184 の反応式
C(C(CC)CNCC1SC(C2C=C3C(=C(C(N)=O)C=2)NC=C3C2CCN(S(CC)(=O)=O)CC2)=CC=1)C.[CH:37]([C:39]1[S:43][C:42]([B:44]([OH:46])[OH:45])=[CH:41][CH:40]=1)=O.[CH3:47][O:48][CH2:49][CH2:50][CH2:51][NH2:52].[BH3-]C#N.[Na+]>>[CH3:47][O:48][CH2:49][CH2:50][CH2:51][NH:52][CH2:37][C:39]1[S:43][C:42]([B:44]([OH:46])[OH:45])=[CH:41][CH:40]=1

参加物

5

反応物 4

HCID 16723-MethoxypropylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 5003444Sodium cyanoborohydrideHCID 577326215-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

生成物 1

HCID 66722906[5-({[3-(Methyloxy)propyl]amino}methyl)-2-thienyl]boronic acid収率 40.9%

実験手順

Following the general procedure of 5-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), [3-(methyloxy)propyl]amine (29 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[3-(methyloxy)propyl]amino}methyl)-2-thienyl]boronic acid. The crude [5-({[3-(methyloxy)propyl]amino}methyl)-2-thienyl]boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (65 mg, 0.157 mmol), K2CO3 (130 mg, 0.942 mmol), and tetrakis(triphenylphosphine)palladium(0) (9 mg, 0.0079 mmol). The crude product was purified once on an Agilent MDAP using the procedure shown in preparation of 5-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide to give 7.6 mg of the title compound (9%).

後処理

  1. customwere reacted

出典と根拠

ORDレコード
ord-e45433e043cd4222bb0e3804f4098865
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

関連ノート

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