3-Aminophenol → HCID 178426212, compound

HRID 1522128Notes

Reaction equation

HRID 1522128 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.[O:18]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[C:39]([N:41]1[CH2:46][CH2:45][N:44]([CH2:47]/[CH:48]=[CH:49]/[C:50]([OH:52])=O)[CH2:43][CH2:42]1)=[O:40])(C)(C)C.C([CH2:56][CH2:57][C:58]1[N:62]2[B-:63]([F:73])([F:72])[N+:64]3[C:65]([C:67]([CH3:71])=[CH:68][C:69]=3[CH3:70])=[CH:66][C:61]2=[CH:60][CH:59]=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:50](=[O:52])/[CH:49]=[CH:48]/[CH2:47][N:44]3[CH2:43][CH2:42][N:41]([C:39](=[O:40])[CH2:56][CH2:57][C:58]4[N:62]5[B-:63]([F:73])([F:72])[N+:64]6[C:65]([C:67]([CH3:71])=[CH:68][C:69]=6[CH3:70])=[CH:66][C:61]5=[CH:60][CH:59]=4)[CH2:46][CH2:45]3)[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:22]1[CH:23]=[CH:24][C:19]([O:18][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 5

HCID 115683-AminophenolHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092896(E)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)but-2-enoic acidHCID 178426214HCID 178426214, compound

Product 1

HCID 178426212HCID 178426212, compound

Procedure

(E)-7-(3-(4-(4-((3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)amino)-4-oxobut-2-en-1-yl)piperazin-1-yl)-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-phenoxyphenyl)boronic acid, (E)-4-(4-(tert-butoxycarbonyl)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, B, E, D, and E. HPLC purity: 100%. MS: m/z=797 [M+H]+.

Sources & evidence

ORD record
ord-ea92195cb9454ed8a52df4993c27a8f2
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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