Sodium hydride → 6-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-(3-hydroxy-propyl)-pyridine-2-carboxylic acid

HRID 1518395노트

반응식

HRID 1518395 반응식
CN1CCN(CCCNC2N=CN=C3N(C4C=CC([OH:27])=CC=4)N=CC=23)CC1.[H-].[Na+].[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[NH:39][C:40]([C:42]1[CH:43]=[CH:44][CH:45]=[C:46]2[C:51]=1[CH2:50][N:49]([C:52]1[N:57]=[C:56]([C:58]([O:60]C(C)(C)C)=[O:59])[C:55]([CH2:65][CH2:66][CH2:67]I)=[CH:54][CH:53]=1)[CH2:48][CH2:47]2)=[O:41]>CN(C=O)C>[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[NH:39][C:40]([C:42]1[CH:43]=[CH:44][CH:45]=[C:46]2[C:51]=1[CH2:50][N:49]([C:52]1[N:57]=[C:56]([C:58]([OH:60])=[O:59])[C:55]([CH2:65][CH2:66][CH2:67][OH:27])=[CH:54][CH:53]=1)[CH2:48][CH2:47]2)=[O:41]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 594474634-(4-(3-(4-methylpiperazin-1-yl)propylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenolHCID 59447593tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-iodopropyl)picolinate

생성물 1

HCID 468369296-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-(3-hydroxy-propyl)-pyridine-2-carboxylic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 84A (60 mg, 0.163 mmol) in DMF (5 ml) was added sodium hydride (32.7 mg, 0.816 mmol)(60%). The reaction was stirred for 10 min and compound 96D (107 mg, 0.163 mmol) was added. The resulting mixture was stirred for 3 hour and purified by reverse phase HPLC (mobile phase: 0%-50% acetonitrile in 0.1% TFA aqueous solution during 70 min) to provide the title compound 99: 1H NMR (400 MHz, DMSO-D6) δ ppm 12.81 (1H, s), 8.04 (1H, dd), 7.79 (1H, d), 7.60 (1H, d), 7.53 (1H, d), 7.45-7.50 (1H, m), 7.39-7.43 (1H, m), 7.32-7.38 (2H, m), 6.95 (1H, d), 4.92 (2H, s), 3.86 (2H, t), 3.37 (2H, t), 2.99 (2H, t), 2.63-2.70 (2H, m), 1.58-1.69 (2H, m), LCMS (APCI) 489 (M+H).

후처리

  1. stirringThe resulting mixture was stirred for 3 hour
  2. custompurified by reverse phase HPLC (mobile phase: 0%-50% acetonitrile in 0.1% TFA aqueous solution during 70 min)

출처 및 근거

ORD 기록
ord-a3764d17e1be41318c175c370e657ee8
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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