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

HRID 1806370노트

반응식

HRID 1806370 반응식
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

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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%).

후처리

  1. customwere reacted

출처 및 근거

ORD 기록
ord-74453f6e578647d78d4d538ae74d8e10
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

반응 노트

불러오는 중…