tert-Butyl carbamate → {1-[4-(7-Amino-8-methylamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037367Notes

Reaction equation

C(OC(=O)N)(C)(C)C.[C:9]([O:13][C:14](=[O:48])[NH:15][C:16]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([NH:40][CH3:41])[C:31]([N+:37]([O-])=O)=[CH:32][CH:33]=4)[O:28][C:27]=3[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10]>>[C:9]([O:13][C:14](=[O:48])[NH:15][C:16]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([NH:40][CH3:41])[C:31]([NH2:37])=[CH:32][CH:33]=4)[O:28][C:27]=3[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1)([CH3:12])([CH3:10])[CH3:11]

Participants

Reactant 2

HCID 77922tert-Butyl carbamate

HCID 67067957{1-[4-(8-methylamino-7-nitro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067881{1-[4-(7-Amino-8-methylamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl esterYield 89%

Procedure

Following the procedure used to prepare 1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, {1-[4-(8-methylamino-7-nitro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a yellow oil (95 mg, 89%). LCMS (Method H): RT=3.69 min, [M+H]+=512.

Workup

customwas reacted

Sources & evidence

ORD record: ord-b9b12c737d484b238d4d8d7f66697494
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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