4-[7-(2-Morpholin-4-yl-2-oxo-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester → 4-[7-(2-Morpholin-4-yl-2-oxo-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide

HRID 657274Notes

Reaction equation

HRID 657274 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH2:25][C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[N+](C1C=CC(OC(=O)[NH:46][C:47]2[CH:52]=[CH:51][C:50]([N:53]3[CH2:57][CH2:56][CH2:55][CH2:54]3)=[CH:49][CH:48]=2)=CC=1)([O-])=O>>[N:53]1([C:50]2[CH:51]=[CH:52][C:47]([NH:46][C:6]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]4[C:23]5[C:18](=[CH:19][C:20]([O:24][CH2:25][C:26]([N:28]6[CH2:33][CH2:32][O:31][CH2:30][CH2:29]6)=[O:27])=[CH:21][CH:22]=5)[N:17]=[CH:16][N:15]=4)[CH2:12][CH2:13]3)=[O:5])=[CH:48][CH:49]=2)[CH2:54][CH2:55][CH2:56][CH2:57]1

Participants

3

Reactant 2

HCID 595517004-[7-(2-Morpholin-4-yl-2-oxo-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl esterHCID 68891845HCID 68891845, compound

Product 1

HCID 587707104-[7-(2-Morpholin-4-yl-2-oxo-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide

Procedure

The title compound was prepared from 4-[7-(2-Morpholin-4-yl-2-oxo-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester as synthesized in the previous step, using (4-pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride (preparation given in Example 74a), essentially as described in Example 170c. 1H-NMR (400 MHz, CDCl3) δ 9.14 (s, 1H), 8.10 (d, 1H), 7.38 (dd, 1H), 7.29 (d, 1H), 7.18 (m, 2H), 6.51 (m, 2H), 6.34 (s, 1H), 4.88 (s, 2H), 4.26 (m, 2H), 3.75-3.61 (m, 7H), 3.55 (m, 2H), 3.25 (m, 4H), 3.10 (td, 2H), 2.16-2.04 (m, 2H), 2.02-1.90 (m, 6H). LC/MS (ESI): calcd mass 544.3, found 545.3 (MH)+.

Workup

  1. customas synthesized in the previous step

Sources & evidence

ORD record
ord-c034e3fca76f4c6c8384e65c23afb5a5
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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