4-(6-Fluoro-7-morpholin-4-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester → 4-(6-Fluoro-7-morpholin-4-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide

HRID 657290Notes

Reaction equation

HRID 657290 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]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]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:43][C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:46][CH:45]=2)=CC=1)([O-])=O>>[N:50]1([C:47]2[CH:48]=[CH:49][C:44]([NH:43][C:6]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]4[C:23]5[C:18](=[CH:19][C:20]([N:25]6[CH2:30][CH2:29][O:28][CH2:27][CH2:26]6)=[C:21]([F:24])[CH:22]=5)[N:17]=[CH:16][N:15]=4)[CH2:12][CH2:13]3)=[O:7])=[CH:45][CH:46]=2)[CH2:51][CH2:52][CH2:53][CH2:54]1

Participants

3

Reactant 2

HCID 595517374-(6-Fluoro-7-morpholin-4-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl esterHCID 68891845HCID 68891845, compound

Product 1

HCID 587706524-(6-Fluoro-7-morpholin-4-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide

Procedure

The title compound was prepared from 4-(6-Fluoro-7-morpholin-4-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester, prepared as described in Example 210a, and (4-pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride, prepared as described in Example 74a, using essentially the protocol given for Example 170c. 1H-NMR (400 MHz, CDCl3) δ 9.12 (s, 1H), 7.70 (d, 1H), 7.38 (d, 1H), 7.18 (m, 2H), 6.52 (m, 2H), 6.24 (s, 1H), 4.26 (m, 2H), 3.93 (m, 4H), 3.51 (tt, 1H), 3.31 (m, 4H), 3.26 (m, 4H), 3.11 (td, 2H), 2.17-2.05 (m, 2H), 2.03-1.90 (m, 6H). LC/MS (ESI): calcd mass 504.3, found 505.3.

Workup

  1. customprepared
  2. customprepared

Sources & evidence

ORD record
ord-a97262a4ed6a4e03bf911f630d76604b
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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