1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-butyl (1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

HRID 1037416Notes

Reaction equation

HRID 1037416 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[C:13](C)=[N:14][N:15]([CH3:18])[C:16]=3[CH3:17])[N:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:3]1[C:26]1[CH:31]=[CH:30][C:29]([C:32]2([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1.ClC1N=CC=C2C(=O)C(C3C=CC(C4(NC(=O)OC(C)(C)C)CCC4)=CC=3)=C(C3C=CC=CC=3)OC=12.CN1C(C)=C(B2OC(C)(C)C(C)(C)O2)C=N1>>[CH3:18][N:15]1[C:16]([CH3:17])=[C:12]([C:7]2[N:8]=[CH:9][CH:10]=[C:11]3[C:2](=[O:1])[C:3]([C:26]4[CH:27]=[CH:28][C:29]([C:32]5([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][CH2:33]5)=[CH:30][CH:31]=4)=[C:4]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:5][C:6]=23)[CH:13]=[N:14]1

Participants

4

Reactant 3

HCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamateHCID 86671060tert-butyl (1-(4-(4-oxo-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 68227656tert-butyl (1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamateYield 82%

Procedure

Following the procedure used to prepare tert-butyl (1-(4-(4-oxo-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate, tert-butyl (1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted with 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to give the title compound (46 mg, 82%). LCMS (Method I): RT=7.35 min, [M+H]+=563.

Sources & evidence

ORD record
ord-5cc555e82f344faa85d18a08c0d8104a
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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