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(Pyrimidin-5-yl)boronic acid → (1E,4E)-2-amino-N,N-dipropyl-8-(pyrimidin-5-yl)-3H-benzo[b]azepine-4-carboxamide

HRID 38008
Notes
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Reaction equation

HRID 38008 reaction equation
[NH2:1][C:2]1[CH2:3][C:4]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])=[CH:5][C:6]2[CH:12]=[CH:11][C:10](Br)=[CH:9][C:7]=2[N:8]=1.[N:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25][CH:24]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+]>O.CC#N>[NH2:1][C:2]1[CH2:3][C:4]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([C:27]3[CH:28]=[N:23][CH:24]=[N:25][CH:26]=3)=[CH:9][C:7]=2[N:8]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateHCID 66961446(1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide

Product 1

HCID 50905000(1E,4E)-2-amino-N,N-dipropyl-8-(pyrimidin-5-yl)-3H-benzo[b]azepine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 18373917
Acetonitrile--water (1/1)
Solvent

Procedure

The title compound was prepared by the procedure as described in Example 124 (Step F) using (1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide, pyrimidin-5-ylboronic acid, and sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate in H2O-MeCN. MS APCI (+) m/z 364 (M+1) detected; 1H-NMR (400 MHz, CDCl3) d 9.21 (s, 1H), 9.01 (s, 2H), 7.50 (s, 1H), 7.43 (d, 1H), 7.27-7.29 (m, 1H), 6.84 (s, 1H), 3.47 (br s, 4H), 2.84 (s, 2H), 1.63-1.72 (m, 4H), 0.94 (t, 6H).

Sources & evidence

ORD record
ord-2d6078700a0c4d57b37ee89a6a0802cc
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524702B2

Reaction notes

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