(2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(morpholino)methanone → [4-(2-{4-[4-(2-Methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenylamino}-benzooxazol-7-yl)-2-methyl-phenyl]-morpholin-4-yl-methanone

HRID 469830Notes

Reaction equation

HRID 469830 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][O:26][CH3:27])[CH2:20][CH2:19]4)=[C:14]([CH3:28])[CH:13]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:31]=1[C:45]([N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)=[O:46]>>[CH3:27][O:26][CH2:25][CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:8]3[O:9][C:10]4[C:2]([C:34]5[CH:33]=[CH:32][C:31]([C:45]([N:47]6[CH2:48][CH2:49][O:50][CH2:51][CH2:52]6)=[O:46])=[C:30]([CH3:29])[CH:35]=5)=[CH:3][CH:4]=[CH:5][C:6]=4[N:7]=3)=[CH:13][C:14]=2[CH3:28])[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 59392731(2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(morpholino)methanoneHCID 67457843(7-Bromo-benzooxazol-2-yl)-{4-[4-(2-methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenyl}-amine

Product 1

HCID 59144237[4-(2-{4-[4-(2-Methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenylamino}-benzooxazol-7-yl)-2-methyl-phenyl]-morpholin-4-yl-methanone

Procedure

The title compound is prepared from (7-bromo-benzooxazol-2-yl)-{4-[4-(2-methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenyl}-amine and [2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-phenyl]-morpholin-4-yl-methanone using methodology described in the preparation of example 65. The title compound is obtained as an off-white foam. Rt=2.00 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 570 (M+1)+.

Workup

  1. customdescribed in the preparation of example 65

Sources & evidence

ORD record
ord-501fbf14a33b4b818628bc407fbbcfec
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…