Putrescine → N,N'-(butane-1,4-diyl)bis(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)

HRID 1470098

반응식

HRID 1470098 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C[CH2:25][N:26]([CH:30]([CH3:32])C)[CH:27]([CH3:29])C.[CH2:33]([NH2:38])[CH2:34][CH2:35][CH2:36][NH2:37]>C(Cl)(Cl)Cl>[CH2:33]([NH:38][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:32]2[C:4]3[C:29](=[C:10]([Cl:12])[CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH2:27][N:26]([CH3:25])[CH2:30]2)=[CH:15][CH:16]=1)(=[O:22])=[O:21])[CH2:34][CH2:35][CH2:36][NH:37][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:5]2[C:4]3[C:9](=[C:10]([Cl:12])[CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH2:8][N:7]([CH3:13])[CH2:6]2)=[CH:15][CH:16]=1)(=[O:22])=[O:21]

참가 물질

5

반응물 3

HCID 1045PutrescineHCID 81531DiisopropylethylamineHCID 223868894-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-benzenesulfonyl chloride2회

생성물 1

HCID 67459666N,N'-(butane-1,4-diyl)bis(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)수율 13.1%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a solution of 4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (intermediate 10.6) (150 mg, 0.353 mmol) in chloroform (0.706 mL) was added DIEA (182 mg, 1.412 mmol) and a solution of butane-1,4-diamine (15.5 mg, 0.176 mmol) in chloroform (0.176 mL). The reaction was stirred overnight at which point the solvent was removed and the resulting residue brought up in 50% IPA/H2O. Purification by preparative HPLC gave the title compound (18.4 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ7.86 (d, 4H), 7.53 (s, 2H), 7.45 (d, 4H), 6.84 (s, 2H), 4.73 (m, 3H), 4.46 (d, 2H), 3.86 (dd, 2H), 3.57 (t, 2H), 3.12 (s, 6H), 2.84 (m, 4H), 1.41 (m, 4H). MS (m/z): 797.15 (M+H).

후처리

  1. customwas removed
  2. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-5460b45abda14ee6852f3fd3078038f3
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006281B2

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