Sodium Chloride → HCID 18768042, compound

HRID 480010Notes

Reaction equation

HRID 480010 reaction equation
Cl.CN(C)CCCN=C=NCC.[Br:13][C:14]1[C:15]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[N:16][C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][CH:22]=2)=[N:18][CH:19]=1.[NH2:38][CH2:39][CH2:40][CH2:41][N:42]1[CH2:46][CH2:45][CH2:44][C:43]1=[O:47].ON1C2C=CC=CC=2N=N1.[Cl-].[Na+]>CN(C=O)C.O>[Br:13][C:14]1[C:15]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[N:16][C:17]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27](=[O:28])[NH:38][CH2:39][CH2:40][CH2:41][N:42]3[CH2:46][CH2:45][CH2:44][C:43]3=[O:47])=[CH:25][CH:26]=2)=[N:18][CH:19]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 757711-HydroxybenzotriazoleHCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9952986HCID 9952986, compound

Product 1

HCID 18768042HCID 18768042, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (52 mg, 0.27 mmol) was added to a mixture of 5-bromo-2-(4-carboxyanilino)-4-(4-fluoroanilino)pyrimidine (Method 7; 100 mg, 0.25 mmol), N-(3-aminopropyl)-2-pyrrolidinone (38 mg, 0.27 mmol) and 1-hydroxybenzotriazole (44 mg, 0.32 mmol) in DMF (0.5 ml). The mixture was stirred for 16 hours and then a 1:1 mixture of saturated sodium chloride solution and water (10 ml) was added. The precipitated solid was collected by filtration and dried to a constant weight in a vacuum oven at 40° C. to give the product as an off-white solid (98 mg, 75%). MS (MH+): 528; HPLC (RT): 4.01.

Workup

  1. additionwas added
  2. filtrationThe precipitated solid was collected by filtration
  3. customdried to a constant weight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-2e66ae62785c42ada029df0ab253810e
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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