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

HRID 657285Notes

Reaction equation

HRID 657285 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:25][CH2:26][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)=[C:21]([F:24])[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:48][C:49]2[CH:54]=[CH:53][C:52]([N:55]3[CH2:60][CH2:59][O:58][CH2:57][CH2:56]3)=[CH:51][CH:50]=2)=CC=1)([O-])=O>>[N:55]1([C:52]2[CH:51]=[CH:50][C:49]([NH:48][C:6]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]4[C:23]5[C:18](=[CH:19][C:20]([O:25][CH2:26][CH2:27][CH2:28][N:29]6[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]6)=[C:21]([F:24])[CH:22]=5)[N:17]=[CH:16][N:15]=4)[CH2:12][CH2:13]3)=[O:7])=[CH:54][CH:53]=2)[CH2:56][CH2:57][O:58][CH2:59][CH2:60]1

Participants

3

Reactant 2

HCID 595517194-{6-Fluoro-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 587706564-{6-Fluoro-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-Fluoro-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 9.14 (s, 1H), 7.74 (d, 1H), 7.44 (d, 1H), 7.27 (m, 2H), 6.88 (m, 2H), 6.32 (s, 1H), 4.27 (m, 4H), 3.86 (m, 4H), 3.54 (tt, 1H), 3.18-3.08 (m, 6H), 2.58 (t, 2H), 2.64-2.35 (br, 8H), 2.30 (s, 3H), 2.12 (m, 4H), 1.96 (m, 2H). LC/MS (ESI): calcd mass 591.3, found 592.4 (MH)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-bfa3d2b22780492fbfe9a76ba1d9a7c8
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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