1H-Indole-2-carboxylic acid, 1-methyl- → HCID 178432917, 화합물

HRID 245744

반응식

HRID 245744 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=1)=[O:12].CN1C2C(=CC=CC=2)C=C1C(O)=O.CC1(C)C(C)(C)OB(C2C=CC(N)=CC=2)O1.Br[C:59]1[N:60]=[C:61]([C@H:69]2[CH2:74][CH2:73][C@H:72]([N:75]3[CH2:80][CH2:79][N:78]([CH3:81])[CH2:77][CH2:76]3)[CH2:71][CH2:70]2)[N:62]2[CH:67]=[CH:66][N:65]=[C:64]([CH3:68])[C:63]=12>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:59]2[N:60]=[C:61]([C@H:69]3[CH2:74][CH2:73][C@H:72]([N:75]4[CH2:80][CH2:79][N:78]([CH3:81])[CH2:77][CH2:76]4)[CH2:71][CH2:70]3)[N:62]3[CH:67]=[CH:66][N:65]=[C:64]([CH3:68])[C:63]=23)=[CH:16][CH:15]=1)=[O:12]

참가 물질

5

반응물 4

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 184505431-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamideHCID 178432912HCID 178432912, 화합물

생성물 1

HCID 178432917HCID 178432917, 화합물수율 27.9%

실험 절차

Reaction of 1-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide (29 mg), prepared from 1-methyl-1H-indole-2-carboxylic acid which was transformed into its acid chloride first and then reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (30 mg) according to the procedure described in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol) gave 1-methyl-N-(4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-indole-2-carboxamide (12 mg)

후처리

  1. customdescribed in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol)

출처 및 근거

ORD 기록
ord-448dea8b6c55473c849f56cd0dd53cd5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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