(4-(Aminomethyl)phenyl)boronic acid → HCID 71744727, compound

HRID 1844341Notes

Reaction equation

HRID 1844341 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:7][C:6]=12.[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>>[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C@@H:13]4[CH2:17][CH2:16][CH2:15][N:14]4[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:7][C:6]=23)=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 86697430HCID 86697430, compound

Product 1

HCID 71744727HCID 71744727, compoundYield 73%

Procedure

The Suzuki coupling of (5)-tert-butyl 2-(((3-bromopyrazolo[1,5-a]pyrimidin-5-yl)amino)methyl)pyrrolidine-1-carboxylate with (4-(aminomethyl)phenyl)boronic acid under the same conditions as described in example 5.6.5 to give 73% of the titled compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.44 (br. s., 9 H) 1.90 (dd, J=9.92, 5.51 Hz, 1 H) 1.96-2.11 (m, 3 H) 3.35-3.45 (m, 4 H) 4.07-4.21 (m, 3 H) 6.33 (br. s., 1 H) 7.46 (d, J=8.38 Hz, 2 H) 8.19 (br. s., 2 H) 8.25-8.36 (m, 2 H); LRMS (ESI) m/e 423.0 [(M+H)+, calcd for C23H30N6O2 422.0].

Sources & evidence

ORD record
ord-56cd12332e014edc94e626c42e09b1fd
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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