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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 1802019
Notes
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Reaction equation

HRID 1802019 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574718944-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylic acid

Product 1

HCID 57471896
4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-(1H-benzo[d][1,2,3]triazol-1-yloxy)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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

  1. stirringstirred the mixture at room temperature for 18 h
  2. customto precipitate iv
  3. customCollected it
  4. filtrationby filtration
  5. washrinsed with water, and air
  6. customdried

Sources & evidence

ORD record
ord-2aaf01ae846143d0bcebe53d63a3a6ae
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349860B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes