Monobenzone → [2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

HRID 1518357Notes

Reaction equation

HRID 1518357 reaction equation
NC1N(C(OC(C)(C)C)=O)N=C([C:14]2[CH:67]=[CH:66][C:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23](C4SC(N5CCC6C(=C(C(=O)N(C7SC8C=CC=CC=8N=7)COCC[Si](C)(C)C)C=CC=6)C5)=NC=4C(OCC)=O)=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)C=1C#N.NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(O)=CC=2)C=1C#N.[CH3:92][N:93]([CH3:97])[CH2:94][CH2:95][OH:96].C(OC1C=CC(O)=CC=1)C1C=CC=CC=1>>[CH2:19]([O:18][C:17]1[CH:16]=[CH:15][C:14]([O:96][CH2:95][CH2:94][N:93]([CH3:97])[CH3:92])=[CH:67][CH:66]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 7638MonobenzoneHCID 79022-(Dimethylamino)ethanolHCID 59447596ethyl 5-(4-((4-(5-amino-1-(tert-butoxycarbonyl)-4-cyano-1H-pyrazol-3-yl)phenoxy)methyl)phenyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylateHCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 59447665[2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

Procedure

Compound 75A was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34D and compound 31F with 2-(dimethylamino)ethanol and 4-(benzyloxy)phenol, respectively: 1H NMR (DMSO-d6): δ 7.31-7.44 (m, 5H), 6.84-6.94 (m, 4H), 5.03 (s, 2H), 3.94-3.98 (m, 2H), 2.57 (d, J=5.93 Hz, 2H), 2.19 (s, 6H). ESI (+)/MS: 272 (M+H)+.

Sources & evidence

ORD record
ord-3cc6366269ed4effb151370eba6cb96e
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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