4-Hydrazinyl-2-methylbenzonitrile hydrochloride → 2-(4-Cyano-3-methylphenyl)-3-isopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid

HRID 505738노트

반응식

HRID 505738 반응식
[CH3:1][CH:2]([CH3:19])[CH:3]=[C:4]1[C:13](=O)[C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17]C)=[O:16])=[CH:10][CH:11]=2)[O:6][CH2:5]1.Cl.[NH:21]([C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([CH3:31])[CH:24]=1)[NH2:22]>>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([N:21]2[CH:3]([CH:2]([CH3:19])[CH3:1])[CH:4]3[CH2:5][O:6][C:7]4[CH:8]=[C:9]([C:15]([OH:17])=[O:16])[CH:10]=[CH:11][C:12]=4[C:13]3=[N:22]2)=[CH:24][C:25]=1[CH3:31])#[N:28]

참가 물질

3

반응물 2

HCID 469150334-Hydrazinyl-2-methylbenzonitrile hydrochlorideHCID 66722771Methyl 3-(2-methylpropylidene)-4-oxochroman-7-carboxylate

생성물 1

HCID 594293192-(4-Cyano-3-methylphenyl)-3-isopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid수율 52%

실험 절차

The title compound was prepared from methyl 3-(2-methylpropylidene)-4-oxochroman-7-carboxylate (Preparation 32; 260 mg, 1.0 mmol) and 4-hydrazinyl-2-methylbenzonitrile hydrochloride (Preparation 2; 275 mg, 1.5 mmol) according to Method B and Method C (yellow solid, 196 mg, 0.523 mmol, 52% yield, approximately 7:1 mixture of cis:trans diastereomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.12 (br. s., 1H), 7.93 (d, J=8.2 Hz, 1H), 7.58 (dd, J=8.2, 1.6 Hz, 1H), 7.55 (d, J=8.6 Hz, 1H), 7.46 (d, J=1.6 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 7.09 (dd, J=8.6, 2.3 Hz, 1H), 4.76-4.86 (m, 2H), 4.42 (dd, J=13.1, 10.4 Hz, 1H), 4.02 (ddd, J=13.2, 10.6, 5.9 Hz, 1H), 2.42 (s, 3H), 2.06-2.17 (m, 1H), 0.83 (d, J=7.4 Hz, 3H), 0.81 (d, J=7.4 Hz, 3H). ES-MS m/z 376 (M+H).

후처리

  1. additionyellow solid, 196 mg, 0.523 mmol, 52% yield, approximately 7:1 mixture of cis

출처 및 근거

ORD 기록
ord-8f30cfd78151410a8b33715ae45e0ff0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781428B2

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