Ammonia → 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-(1H-benzo[d][1,2,3]triazol-1-yloxy)pyrimidine-5-carboxamide

HRID 1880286Notes

Reaction equation

[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=[C:15](Cl)[N:14]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[CH:23]1[CH:24]=[CH:25][C:26]2[N:31]([OH:32])[N:30]=[N:29][C:27]=2[CH:28]=1.CC[N:35]=C=NCCCN(C)C.Cl.N.O1CCOCC1>CN(C=O)C.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13]3[C:18]([C:19]([NH2:35])=[O:21])=[CH:17][N:16]=[C:15]([O:32][N:31]4[C:26]5[CH:25]=[CH:24][CH:23]=[CH:28][C:27]=5[N:29]=[N:30]4)[N:14]=3)=[CH:10][CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylic acid (iii) (730 mg, 2.305 mmol) in DMF (15 mL), at room temperature, was added HOBt (470 mg, 3.478 mmol, 1.508 equiv), and EDC.HCl (690 mg, 3.599 mmol, 1.561 equiv), and the mixture was stirred for 45 minutes. Then cooled it to 0° C., and treated with 0.5 M NH3 in dioxane (14.0 ml, 7.0 mmol, 3.0 equiv), and stirred the mixture at room temperature for 18 h. Then diluted it with water (7×) to precipitate iv. Collected it by filtration, rinsed with water, and air dried; yield 841 mg (88%). MS: 415.1 (M+H), and 437.1 (M+Na).

Workup

stirringstirred the mixture at room temperature for 18 h
customto precipitate iv
customCollected it
filtrationby filtration
washrinsed with water, and air
customdried

Sources & evidence

ORD record: ord-ee511052a4094254a993a4922df13995
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318755B2

Reaction notes

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