Benzaldehyde → N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide

HRID 252704노트

반응식

HRID 252704 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].Cl[Si](C)(C)C>CN1C(=O)CCC1.C(O)(=O)C>[CH2:19]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

생성물 1

HCID 11501639N-{5-[5-(Benzylamino)-6-chloropyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide수율 46.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (30 mg, 0.11 mmol), benzaldehyde (0.016 mL, 0.16 mmol) and sodium cyanoborohydride (13 mg, 0.21 mmol) were mixed in NMP (0.9 mL) and acetic acid (0.1 mL). Chlorotrimethylsilane (0.04 mL, 0.32 mmol) was added and the mixture was stirred overnight. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 9.73 minutes; 19 mg); 1H NMR Spectrum: (DMSOd6) 12.13 (1H, s); 7.60 (1H, d); 7.38-7.30 (4H, m); 7.22 (1H, t); 6.80 (1H, d); 6.67 (1H, s); 4.47 (2H, s); 2.12 (3H, s); 2.03 (3H, s); Mass Spectrum: M+H+ 373 and 375.

후처리

  1. customThe reaction product was purified by preparative HPLC (Method A)

출처 및 근거

ORD 기록
ord-41f9b66c677d4434bd97f9876f554b7f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868188B2

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