1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4'-(2-(4-Cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxamide

HRID 386637Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH3:19])=[C:12]([O:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]4[CH:33]=[CH:32][C:31]([C:34](O)=[O:35])=[CH:30][CH:29]=4)=[CH:23][C:22]=3[CH3:37])[N:11]=2)=[CH:5][CH:4]=1)#[N:2].C1C=[N:42]C2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[Cl-].[NH4+]>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH3:19])=[C:12]([O:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([NH2:42])=[O:35])=[CH:32][CH:33]=4)=[CH:23][C:22]=3[CH3:37])[N:11]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4′-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3′,5′-dimethylbiphenyl-4-carboxylic acid (40 mg, 0.082 mmol), HOAt (23 mg, 0.18 mmol), and EDCI (35 mg, 0.18 mmol) was added ammonium chloride (25 mg, 0.47 mmol) followed by TEA (0.1 mL, 0.72 mmol) at rt. The reaction mixture was heated at 80° C. for 1 h and added H2O. The solid material which precipitated was collected by filtration and purified on silica gel preparative TLC to yield the desired compound. NMR (DMSO-d6): δ 10.10 (s, 1H), 8.25 (s, 1H), 8.08 (s, 1H), 8.03 (d, 2H), 7.87 (d, 2H), 7.66 (s, 2H), 7.62 (d, 2H), 7.43 (s, 1H), 7.35 (d, 2H), 3.80 (s, 3H), 2.18 (s, 6H); MS (ESI): m/z 490 (M+1)+.

Workup

customThe solid material which precipitated
filtrationwas collected by filtration
custompurified on silica gel preparative TLC

Sources & evidence

ORD record: ord-5e9d97b8150d4e1db6a6eafb0675c097
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372852B2

Reaction notes

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