HCID 3626675, compound → HCID 56924069, compound

HRID 2189243Notes

Reaction equation

HRID 2189243 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[N:18]=[C:17](Cl)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:3]=1.C(OC(N1CCCCC(N)C1)=O)(C)(C)C.[NH2:35][C@@H:36]1[CH2:40][N:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][C@H:37]1[C:48]([O:50][CH2:51][CH3:52])=[O:49]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[N:18]=[C:17]([NH:35][C@@H:36]3[CH2:40][N:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][C@H:37]3[C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:3]=1.[NH2:35][C@@H:36]1[CH2:40][N:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][C@H:37]1[C:48]([O:50][CH2:51][CH3:52])=[O:49]

Participants

5

Reactant 3

HCID 3626675HCID 3626675, compoundHCID 23068067tert-Butyl 3-aminoazepane-1-carboxylateHCID 56924069HCID 56924069, compound

Product 2

HCID 56924069HCID 56924069, compoundHCID 136089391HCID 136089391, compound

Procedure

The title compound was prepared using a method analogous to that described in Synthesis 52, replacing 4-chloro-2-(2-methoxyphenyl)quinazoline with 4-bromo-2-(4-chloroquinazolin-2-yl)phenol and tert-butyl-3-aminoazepane-1-carboxylate with (3R,4S)-1-tert-butyl 3-ethyl 4-aminopyrrolidine-1,3-dicarboxylate. (3R,4S)-1-tert-Butyl 3-ethyl 4-aminopyrrolidine-1,3-dicarboxylate was prepared as described in J. Am. Chem. Soc., 2006, 10638.

Workup

  1. customthat described in Synthesis 52

Sources & evidence

ORD record
ord-9d7f0ef8abd0416aa9e567667a617755
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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