Cyclopropylboronic acid → 4-(5-Cyano-7-cyclopropyl-1,3-benzoxazol-2-yl)-N-({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)benzamide

HRID 2093647Notes

Reaction equation

Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([C:37]#[N:38])[CH:3]=1.[CH:39]1(B(O)O)[CH2:41][CH2:40]1>>[C:37]([C:4]1[CH:3]=[C:2]([CH:39]2[CH2:41][CH2:40]2)[C:10]2[O:9][C:8]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:20][CH2:21][N:22]([C:25]5[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=5)[CH2:23][CH2:24]4)=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1)#[N:38]

Participants

Reactant 2

HCID 2760897Cyclopropylboronic acid

HCID 687416644-(7-Bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)benzamide

Product 1

HCID 251726714-(5-Cyano-7-cyclopropyl-1,3-benzoxazol-2-yl)-N-({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)benzamide

Procedure

The title compound was prepared from 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)benzamide (EXAMPLE 114, Step B) and cyclopropylboronic acid by a procedure analogous to that described in EXAMPLE 117. Mass spectrum (ESI) 546.3 (M+1). 1H NMR (500 MHz, CDCl3) δ: 8.38 (s, 1H), 8.33 (d, J=8.3 Hz, 2H), 7.95 (d, J=8.1 Hz, 2H), 7.86 (s, 1H), 7.60 (br d, J=8.9 Hz, 1H), 7.23 (s, 1H), 6.65 (d, J=8.9 Hz, 1H), 6.38 (br s, 1H), 4.46 (d, J=13.1 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 2.93 (t, J=12.1 Hz, 2H), 2.33 (m, 1H), 2.00 (m, 1H), 1.90 (d, J=12.3 Hz, 2H), 1.33 (m, 2H), 1.22 (m, 2H), 1.06 (m, 2H).

Sources & evidence

ORD record: ord-ccfdaa42bbfd417e947138c1518f961e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

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