Sodium Bicarbonate → HCID 178482433, 화합물

HRID 2416057노트

반응식

HRID 2416057 반응식
[CH3:1][NH:2][C:3]1[S:4][C:5](=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[C:6](=[O:8])[N:7]=1.[OH:23][C@@H:24]([CH2:37][NH2:38])[CH2:25][O:26][C:27]1[C:35]2[NH:34][C:33](=[O:36])[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(O)(=O)C>[OH:23][C@@H:24]([CH2:37][NH:38][CH:19]1[CH2:20][CH2:21][N:16]([C:13]2[CH:14]=[CH:15][C:10]([CH:9]=[C:5]3[S:4][C:3]([NH:2][CH3:1])=[N:7][C:6]3=[O:8])=[CH:11][CH:12]=2)[CH2:17][CH2:18]1)[CH2:25][O:26][C:27]1[C:35]2[NH:34][C:33](=[O:36])[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 1784824352-(methylamino)-5-[[4-(4-oxopiperidin-1-yl)phenyl]methylidene]-1,3-thiazol-4-one2회

생성물 1

HCID 178482433HCID 178482433, 화합물수율 65.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

실험 절차

1-[4-(2-Methylamino-4-oxo-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one (which was obtained in Intermediate 18)(0.15 g, 0.47 mmol) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (Jesudason, C. D., et al., EP 0 764 640) (0.11 g, 0.47 mmol) were mixed in dimethylformamide (15 mL) and then treated with sodium triacetoxyborohydride (0.16 g, 0.75 mmol) and acetic acid (0.15 mL). After stirring at room temperature under a nitrogen atmosphere for one day the mixture was poured into a saturated aqueous sodium bicarbonate solution. The precipitate was collected and purified by column chromatography (eluent: methanol/methylene chloride) to give the title compound as a pale yellowish solid(0.16 g, 65%); mp>160° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.45 (m, 2 H), 1.75-2.00 (m, 2 H), 2.60-3.00 (m, 5 H), 3.05 (s, 3 H), 3.75-4.15 (m, 5 H), 6.57 (d, J=7.8 Hz, 1 H), 6.62 (d, J=8.1 Hz, 1 H), 6.87 (t, J=8.1 Hz, 1 H), 7.02 (d, J=8.7 Hz, 2 H), 7.38 (d, J=8.7 Hz, 2 H), 7.47 (s, 1 H), 10.56 (s, 1 H), 10.70 (brs, 1 H); MS (ES) m/z: 262.1 ((M+2H)2+, 100%); 522.9 (MH+, 75%); HRMS Calcd. for C26H31N6O4S (MH+): 523.2128. Found: 523.2142.

후처리

  1. customThe precipitate was collected
  2. custompurified by column chromatography (eluent: methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-704f13972917404aa841606a050363c9
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821991B2

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