Triethylamine → HCID 178498196, 화합물

HRID 1056480노트

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HRID 1056480 반응식
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:4][C:3]=1[CH:17]([CH3:19])[CH3:18].F[P-](F)(F)(F)(F)F.N1([PH+](N2CCCC2)N2CCCC2)CCCC1.[Cl-].[CH3:44][O:45][C:46]([C:48]1[CH:53]=[CH:52][C:51]([N:54]=[N:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][NH3+:63])=[CH:58][CH:57]=2)=[CH:50][CH:49]=1)=[O:47].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[OH:1][C:2]1[C:3]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:5]([CH2:11][CH2:12][CH2:13][C:14]([NH:63][CH2:62][C:59]2[CH:58]=[CH:57][C:56](/[N:55]=[N:54]/[C:51]3[CH:52]=[CH:53][C:48]([C:46]([O:45][CH3:44])=[O:47])=[CH:49][CH:50]=3)=[CH:61][CH:60]=2)=[O:16])=[CH:6][C:7]=1[CH:8]([CH3:9])[CH3:10]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 22226026Tripyrrolidinophosphonium hexafluorophosphateHCID 568512964-(4-Hydroxy-3,5-diisopropylphenyl)butanoic acidHCID 86695989(4-((4-(Methoxycarbonyl)phenyl)diazenyl)phenyl)methanaminium chloride

생성물 1

HCID 178498196HCID 178498196, 화합물수율 57.4%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회HCID 21584188Chloroform methanol용매

실험 절차

Acid 8 (164 mg, 1.00 mmol), benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (BOP, 884 mg, 2.00 mmol) and DMAP (12 mg, 0.10 mmol) were dissolved in methylene chloride (10 mL) and stirred at room temperature for 10 min. A solution of compound 4 (366 mg, 1.2 mmol) and triethylamine (505 mg, 5.0 mmol) in methylene chloride (15 mL) was added, and the reaction mixture was stirred at room temperature for 48 h. Aqueous work-up and chromatography on silica gel using chloroform and chloroform-methanol (3%) step-gradient as an eluent afforded pure 9 (296 mg, 57%) as orange crystals. 1H NMR (360 MHz, CDCl3): δ 8.18 (d, J=8.6 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H), 7.91 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.3 Hz, 2H), 6.85 (s, 2H), 5.83 (t, J=9.1 Hz, 1H), 4.73 (s, 1H), 4.53 (d, J=5.9 Hz, 2H), 3.96 (s, 3H), 3.11 (septet, J=6.9 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H), 2.29 (t, J=7.6 Hz, 2H), 1.99 (q, J=7.6 Hz, 2H), 1.24 (d, J=6.9 Hz, 12H). 13C NMR (90.55 MHz, CDCl3): δ 173.23, 166.90, 155.42, 152.23, 148.52, 142.66, 133.99, 133.57, 132.17, 130.98, 128.85, 128.38, 123.87, 123.73, 123.01, 121.65, 120.13, 52.73, 43.56, 36.51, 35.45, 28.02, 27.51, 23.15. HRMS (m/z): [M+H]+ calcd. for C31H37N3O4 516.2857. found 516.2863.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 48 h

출처 및 근거

ORD 기록
ord-a3e69b28956443acb418518a6b453f08
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399145B2

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