Water → N-(2-aminophenyl)-4-((4-(pyrazin-2-yl)pyrimidin-2-ylamino)methyl)benzamide

HRID 416227Notes

Reaction equation

HRID 416227 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[N:8]=1.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH2:30].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>C(#N)C>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:31][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][C:9]2[N:8]=[C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)[CH:12]=[CH:11][N:10]=2)=[CH:23][CH:22]=1

Participants

8

Reactant 6

HCID 962WaterHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid

Product 1

HCID 44570891N-(2-aminophenyl)-4-((4-(pyrazin-2-yl)pyrimidin-2-ylamino)methyl)benzamideYield 55.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 25a (1 g, 3.3 mmol) in dry acetonitrile (35 mL) was added 1,2-phenylenediamine (0.88 g, 8.1 mmol) followed by Et3N (2.7 mL, 19.1 mmol), HOBt.H2O (803 mg, 5.9 mmol) and EDCI.HCl (1.89 g, 9.9 mmol). The mixture was stirred at room temperature for 16 h to form a suspension which was collected by filtration, washed successively with MeCN, water and again MeCN, triturated with MeOH, filtered and dried to afford the title compound 26a (730 mg, 1.84 mmol, 55% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.57 (s, 1H), 9.43 (s, 1H), 8.75 (d, J=4.8 Hz, 2H), 8.49 (d, J=5.2 Hz, 1H), 8.11 (t, J=5.2 Hz, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.59-7.37 (m, 2H), 7.44 (d, J=5.2 Hz, 1H), 7.12 (d, J=7.6 Hz, 1H), 6.94 (td, J=7.6, 1.6 Hz, 1H), 6.75 (dd, J=8.0, 1.2 Hz, 1H), 6.57 (t, J=7.2 Hz, 1H), 4.86 (s, 2H), 4.66 (d, J=5.2 Hz, 2H).

Workup

  1. customto form a suspension which
  2. filtrationwas collected by filtration
  3. washwashed successively with MeCN, water and again MeCN
  4. customtriturated with MeOH
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-43a60525e4074b3caa6df238b2036751
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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