4-{6-Methoxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid tert-butyl ester → 4-{6-Methoxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

HRID 657287Notes

Reaction equation

HRID 657287 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.Cl.[N+](C1C=CC(OC(=O)[NH:49][C:50]2[CH:55]=[CH:54][C:53]([N:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)=[CH:52][CH:51]=2)=CC=1)([O-])=O>>[N:56]1([C:53]2[CH:52]=[CH:51][C:50]([NH:49][C:6]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[C:23]5[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH2:29][N:30]6[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]6)=[C:21]([O:24][CH3:25])[CH:22]=5)[N:17]=[CH:16][N:15]=4)[CH2:10][CH2:9]3)=[O:7])=[CH:55][CH:54]=2)[CH2:57][CH2:58][O:59][CH2:60][CH2:61]1

Participants

3

Reactant 2

HCID 120037984-{6-Methoxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid tert-butyl esterHCID 68947764(4-Morpholin-4-yl-phenyl)-carbamic acid 4-nitrophenyl ester hydrochloride

Product 1

HCID 159805144-{6-Methoxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Procedure

The title compound was prepared from 4-{6-Methoxy-7-[3-(4-methyl-piperazin-1-yl)-propoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid tert-butyl ester, prepared in the previous step, and (4-morpholin-4-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride, prepared as described in Example 66a, using essentially the protocol given for Example 170c. 1H-NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 7.34 (s, 1H), 7.28 (m, 2H), 7.25 (s, 1H), 6.88 (m, 2H), 6.34 (s, 1H), 4.27 (m, 4H), 4.05 (s, 3H), 3.86 (m, 4H), 3.59 (tt, 1H), 3.16 (td, 2H), 3.11 (m, 4H), 2.57 (m, 2H), 2.65-2.34 (br, 8H), 2.30 (s, 3H), 2.21-2.08 (m, 4H), 2.03-1.95 (m, 2H). LC/MS (ESI): calcd mass 603.4, found 604.4 (MH)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-dfedf56afd274703b933e97cca3d9be1
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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