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

HRID 222081Notes

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-910195ca6d944697b0726bd27eb86d17
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207178B2

Reaction notes

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