HCID 58189084, compound → HCID 52920370, compound

HRID 1423106Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[C:4]([O:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1.[N:17]1([CH2:22][C@H:23]2[CH2:28][NH:27][CH2:26][CH2:25][N:24]2C(OC(C)(C)C)=O)[CH:21]=[CH:20][CH:19]=[N:18]1>>[N:17]1([CH2:22][C@@H:23]2[NH:24][CH2:25][CH2:26][N:27]([C:2]3[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[C:4]([O:11][CH:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)[CH:3]=3)[CH2:28]2)[CH:21]=[CH:20][CH:19]=[N:18]1

Participants

Reactant 2

HCID 58189084HCID 58189084, compound

HCID 66825877HCID 66825877, compound

Product 1

HCID 52920370HCID 52920370, compound

Procedure

The title compound was prepared by the method outlined for Example 1 using 4-bromo-2-(cyclopentyloxy)-1-ethoxybenzene as the aryl halide and tert-butyl (2R)-2-(1H-pyrazol-1-ylmethyl)piperazine-1-carboxylate as amine component. The intermediate and title compound were isolated as oils (76 and 77%). 1H NMR (CDCl3) 7.55 (d, J=1.6, 1H), 7.43 (d, J=1.9, 1H), 6.80 (d, J=8.6, 1H), 6.53 (d, J=2.8, 1H), 6.42 (dd, J=8.6, 2.7, 1H), 6.26 (t, J=2.2, 1H), 4.76-4.73 (m, 1H), 4.23 (dd, J=13.7, 4.9, 1H), 4.14 (dd, J=13.5, 7.6, 1H), 3.98 (q, J=7.1, 2H), 3.42-3.27 (m, 3H), 3.09 (dt, J=11.8, 3.0, 1H), 2.96 (td, J=10.8, 3.0, 1H), 2.75 (td, J=11.1, 3.1, 1H), 2.49 (t, J=9.6, 1H), 1.89-1.81 (m, 6H), 1.62-1.59 (m, 2H), 1.37 (t, J=6.8, 3H). 13C NMR 149.0, 146.7, 144.0, 139.9 (CH), 130.1 (CH), 116.1 (CH), 108.9 (CH), 107.3 (CH), 105.6 (CH), 80.8, (CH), 65.7 (CH2), 55.1 (CH), 55.0 (CH), 54.4 (CH2), 51.0 (CH2), 45.1 (CH2), 32.8 (CH2), 23.9 (CH2), 15.1 (CH3). LC/MS (Method B) 4.40 and 2.55 min, [M+1]+ 471 and 371.

Workup

customThe title compound was prepared by the method

Sources & evidence

ORD record: ord-8847e4bf85e542db829649935a6a1f36
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927546B2

Reaction notes

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