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

HRID 657254Notes

Reaction equation

HRID 657254 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]([F:24])=[CH:21][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:37][C:38]2[CH:43]=[CH:42][C:41]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:40][CH:39]=2)=CC=1)([O-])=O>>[N:44]1([C:41]2[CH:40]=[CH:39][C:38]([NH:37][C:6]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[C:23]5[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=5)[N:17]=[CH:16][N:15]=4)[CH2:10][CH2:9]3)=[O:7])=[CH:43][CH:42]=2)[CH2:45][CH2:46][O:47][CH2:48][CH2:49]1

Participants

3

Reactant 2

HCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl esterHCID 68947764HCID 68947764, compound

Product 1

HCID 587707764-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Procedure

Prepared essentially as described in Example 67 using 4-(7-fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester and (4-morpholin-4-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride, which was prepared as described in Example 66a. 1H NMR (CDCl3) δ 9.23 (s, 1H), 9.21 (dd, J=9.35 Hz and 5.85 Hz, 1H), 7.69 (dd, J=9.48 and 2.52 Hz, 1H), 7.44 (m, 1H), 7.27 (d, J=8.95 Hz, 2H), 6.89 (d, J=8.95 Hz, 2H), 6.29 (s, 1H), 4.27 (m, 2H), 3.86 (t, J=4.74 Hz, 4H), 3.73 (m, 1H), 3.17 (m, 2H), 3.11 (t, J=4.78 Hz, 4H), 2.15 (m, 2H), 1.99 (m, 2H). Calcd for C24H27FN5O2 (MH+) 436.2, found 436.1.

Workup

  1. customPrepared essentially
  2. customwas prepared

Sources & evidence

ORD record
ord-d457da58cea84105a40fca3fbd0eff51
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

Loading…