3-Aminophenol → HCID 178426213, compound

HRID 1522136Notes

Reaction equation

HRID 1522136 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.F[C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(O[C:40]([NH:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][N:48]([CH2:51]/[CH:52]=[CH:53]/[C:54]([OH:56])=O)[CH2:47][CH2:46]1)=[O:41])(C)(C)C.C([CH2:60][CH2:61][C:62]1[N:66]2[B-:67]([F:77])([F:76])[N+:68]3[C:69]([C:71]([CH3:75])=[CH:72][C:73]=3[CH3:74])=[CH:70][C:65]2=[CH:64][CH:63]=1)(O)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:54](=[O:56])/[CH:53]=[CH:52]/[CH2:51][N:48]3[CH2:47][CH2:46][N:45]([CH2:44][CH2:43][NH:42][C:40](=[O:41])[CH2:60][CH2:61][C:62]4[N:66]5[B-:67]([F:77])([F:76])[N+:68]6[C:69]([C:71]([CH3:75])=[CH:72][C:73]=6[CH3:74])=[CH:70][C:65]5=[CH:64][CH:63]=4)[CH2:50][CH2:49]3)[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:34]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 115683-AminophenolHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 53216757[4-(3-Fluorophenoxy)phenyl]boronic acidHCID 59799013HCID 59799013, compoundHCID 178426214HCID 178426214, compound

Product 1

HCID 178426213HCID 178426213, compound

Procedure

(E)-7-(3-((2-(4-(4-((3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)amino)-4-oxobut-2-en-1-yl)piperazin-1-yl)ethyl)amino)-3-oxopropyl)-5,5-difluoro-1,3-dimethyl-5H-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, (4-(3-fluorophenoxy)phenyl)boronic acid, (E)-4-(4-(2-((tert-butoxycarbonyl)amino)ethyl)piperazin-1-yl)but-2-enoic acid, and 7-(2-carboxyethyl)-5,5-difluoro-1,3-dimethyl-5H-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-4-ium-5-uide using methods A, C, E, D, and E. HPLC purity: 100%. MS: m/z=840 [M+H]+.

Sources & evidence

ORD record
ord-0cf3bd36843c400e9868ba5c1e94da79
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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