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Diisopropylethylamine → (R)-N-(1-(2-Fluoro-5-methyl-4-(methylsulfonamido)phenyl)ethyl)-2h-chromene-3-carboxamide

HRID 1690782
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HRID 1690782 반응식
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[CH2:2]1.Cl.[NH2:15][C@@H:16]([C:18]1[C:23]([F:24])=[CH:22][C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:20]([CH3:30])[CH:19]=1)[CH3:17].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O1CCCC1>[F:24][C:23]1[CH:22]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:20]([CH3:30])=[CH:19][C:18]=1[C@H:16]([NH:15][C:11]([C:3]1[CH2:2][O:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:13])[CH3:17]
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 3223042H-chromene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66718598(R)-N-(4-(1-aminoethyl)-5-fluoro-2-methylphenyl)methanesulfonamide hydrochloride

생성물 1

HCID 58118638
(R)-N-(1-(2-Fluoro-5-methyl-4-(methylsulfonamido)phenyl)ethyl)-2h-chromene-3-carboxamide
수율 38.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2H-chromene-3-carboxylic acid (0.015 g, 0.085 mmol), N-[4-((R)-1-aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (20.00 mg, 0.07 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.032 g, 0.085 mmol) in N,N-dimethylformamide (0.39 g) was added N,N-diisopropylethylamine (0.046 g, 0.35 mmol). Tetrahydrofuran (0.38 g) was added to dilute solution. The reaction was stirred overnight. It was then concentrated and purified by HPLC to obtain the product (10.8 mg, 37%) a solid. m/z=405.1 (M+1). 1H-NMR (400 MHz, DMSO-d) δ 9.19 (s, 1H), 8.61 (d, 1H, J=7.66 Hz), 7.37 (s, 1H), 7.30-7.21 (m, 3H), 7.07 (d, 1H, J=11.41 Hz), 6.96 (dt, 1H, J=7.54 Hz), 6.84 (d, 1H, J=7.81 Hz), 5.25-5.18 (m, 1H), 4.88 (s, 2H), 3.02 (s, 3H), 2.25 (s, 3H), 1.41 (d, 3H, J=7.07 Hz).

후처리

  1. concentrationIt was then concentrated
  2. custompurified by HPLC

출처 및 근거

ORD 기록
ord-4535119cbbdf426bb04f1d5cd0b03595
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153651B2

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