tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate → {1-[4-(2,8-Dioxo-6-phenyl-1,2,3,8-tetrahydro-4,5-dioxa-1-aza-phenanthren-7-yl)-phenyl]cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037414Notes

Reaction equation

HRID 1037414 reaction equation
C(CN1C2C(=CC=C3C(=O)C([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)=C(C4C=CC=CC=4)OC3=2)C=N1)#N.I[C:43]1[C:48](=[O:49])[C:47]2[CH:50]=[CH:51][C:52]3[NH:57][C:56](=[O:58])[CH2:55][O:54][C:53]=3[C:46]=2[O:45][C:44]=1[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.CC1(C)C(C)(C)OB(C2C=CC(C3(NC(=O)OC(C)(C)C)CCC3)=CC=2)O1>>[C:31]([O:30][C:29](=[O:35])[NH:28][C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:43]3[C:48](=[O:49])[C:47]4[C:46](=[C:53]5[C:52](=[CH:51][CH:50]=4)[NH:57][C:56](=[O:58])[CH2:55][O:54]5)[O:45][C:44]=3[C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)=[CH:23][CH:22]=2)[CH2:25][CH2:26][CH2:27]1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 3

HCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamateHCID 670678277-Iodo-6-phenyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dioneHCID 86671057Tert-butyl (1-(4-(1-(cyanomethyl)-6-oxo-8-phenyl-1,6-dihydropyrano[3,2-g]indazol-7-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 67067975{1-[4-(2,8-Dioxo-6-phenyl-1,2,3,8-tetrahydro-4,5-dioxa-1-aza-phenanthren-7-yl)-phenyl]cyclobutyl}-carbamic acid tert-butyl esterYield 52%

Procedure

Following the procedure used to prepare tert-butyl (1-(4-(1-(cyanomethyl)-6-oxo-8-phenyl-1,6-dihydropyrano[3,2-g]indazol-7-yl)phenyl)cyclobutyl)carbamate reacted 8-iodo-9-phenylchromeno[8,7-b][1,4]oxazine-3,7(2H,4H)-dione (150 mg, 0.358 mmol), tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutylcarbamate (170 mg, 0.455 mmol) was reacted to give the title compound (100 mg, 52%). LCMS (Method I): RT=6.87 min, [M+H]+=539.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-b2a17c79690b4ba991975bee860d9047
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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