Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → 1-[6-(3,6-Dihydro-2H-pyran-4-yl)-quinolin-4-yl]-3-pyrazin-2-yl-urea

HRID 1528103Notes

Reaction equation

HRID 1528103 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:14].CC1(C)C(C)(C)OB(C2CCN(C(OC(C)(C)C)=O)CC=2)O1.[O:44]1[CH2:49][CH:48]=[C:47](B2OC(C)(C)C(C)(C)O2)[CH2:46][CH2:45]1>>[O:44]1[CH2:45][CH:46]=[C:47]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[C:5]3[NH:12][C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH2:48][CH2:49]1

Participants

4

Reactant 3

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 248590151-(6-Bromoquinolin-4-yl)-3-(pyrazin-2-yl)urea

Product 1

HCID 575201751-[6-(3,6-Dihydro-2H-pyran-4-yl)-quinolin-4-yl]-3-pyrazin-2-yl-urea

Procedure

The title compound was prepared as described in example 27 step 2, substituting 1-(6-bromo-quinolin-4-yl)-3-(6-trifluoromethyl-pyridin-2-yl)-urea by 1-(6-bromoquinolin-4-yl)-3-(pyrazin-2-yl)urea and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate by 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Sources & evidence

ORD record
ord-914f75b5725d4217b67c6102fa7b1e50
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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