2-Piperidin-2-ylethanol → 4-[7-(2-Piperidin-2-yl-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

HRID 657255Notes

Reaction equation

HRID 657255 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[C:31]5[C:26](=[CH:27][C:28](F)=[CH:29][CH:30]=5)[N:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[CH2:39][CH2:40][OH:41]>>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[C:31]5[C:26](=[CH:27][C:28]([O:41][CH2:40][CH2:39][CH:34]6[CH2:35][CH2:36][CH2:37][CH2:38][NH:33]6)=[CH:29][CH:30]=5)[N:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 151442-Piperidin-2-ylethanolHCID 587707764-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Product 1

HCID 587706334-[7-(2-Piperidin-2-yl-ethoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Procedure

Prepared from 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-morpholin-4-yl-phenyl)-amide, synthesized as described in the previous step, and 2-piperidin-2-yl-ethanol using the protocol described in Example 67a. 1H NMR (CD3OD) δ 9.03 (s, 1H), 8.34 (d, J=9.31 Hz, 1H), 7.37 (dd, J=9.19 and 2.54 Hz, 1H), 7.33 (d, J=2.47 Hz, 1H), 7.26 (d, J=9.06 Hz, 2H), 6.93 (d, J=9.10 Hz, 2H), 4.34 (m, 2H), 4.28 (m, 2H), 3.94 (m, 1H), 3.82 (t, J=4.69 Hz, 4H), 3.16 (m, 2H), 3.08 (t, J=4.78 Hz, 4H), 3.04 (m, 1H), 2.82 (m, 1H), 2.66 (m, 1H), 1.40-2.10 (12H). Calcd for C31H41N6O3 (MH+) 545.3, found 545.1.

Workup

  1. customsynthesized

Sources & evidence

ORD record
ord-29a58f6e82e045e1a609afdb9333bde9
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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