Sodium Bicarbonate → (S)-4-(4-(2-(5-fluoro-1H-indol-1-yl)acetyl)-3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 2043126노트

반응식

HRID 2043126 반응식
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34](O)=[O:35])[CH:28]=[CH:27]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+].Cl.S1C(N)=NC=N1>>[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34]([N:7]1[CH2:6][CH2:5][N:4]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]4[S:19][CH:20]=[CH:21][N:22]=4)(=[O:15])=[O:16])=[CH:10][CH:9]=3)[CH2:3][C@@H:2]1[CH3:1])=[O:35])[CH:28]=[CH:27]2

참가 물질

6

반응물 5

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)HCID 45036900(5-Fluoro-1H-indol-1-yl)acetic acidHCID 59466427HCID 59466427, 화합물

생성물 1

HCID 53627607(S)-4-(4-(2-(5-fluoro-1H-indol-1-yl)acetyl)-3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide수율 53%

실험 절차

Synthesized according to general procedure 9, method B. The reaction was set up with (S)-4-(3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (250 mg, 0.74 mmol), 2-(5-fluoro-1H-indol-1-yl)acetic acid (143 mg, 0.74 mmol), HATU reagent (281 mg, 0.74 mmol), sodium bicarbonate (93 mg, 1.11 mmol), and DMF/CH2Cl2-1/1 (4.0 mL) to obtain the desired amide as a white solid (200 mg, 0.39 mmol, 53% yield). 1H NMR (400 MHz, DMSO-d6) 6 (mixture of rotamers) 7.63-7.59 (m, 2H), 7.35 (s, 1H), 7.30 (dd, J=2.5, 9.9 Hz, 2H), 7.21 (d, J=4.6 Hz, 1H), 7.00 (s, 1H), 6.95 (td, J=9.2, 3.9 Hz, 2H), 6.76 (d, J=4.5 Hz, 1H), 6.43 (d, J=3.0 Hz, 1H), 5.41-5.04 (m, 2H), 4.52 (s, ½H), 4.38 (s, ½H), 4.21-4.05 (m, ½H), 3.93-3.82 (m, ½H), 3.81-3.48 (m, 3H), 1.33 (s, 1.5; H), 1.14 (s, 1.5H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=514.5; tR=3.07 min.

후처리

  1. customSynthesized

출처 및 근거

ORD 기록
ord-49914c75c46647f99160ebfbe56c1a4e
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586589B2

반응 노트

불러오는 중…