Sodium Bicarbonate → HCID 178520191, compound

HRID 230733Notes

Reaction equation

HRID 230733 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[S:28][C:27]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([CH2:38][C:39]([OH:41])=O)=[CH:37][C:31]=3[N:30]=2)=[CH:26][CH:25]=1.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][C:50]2=[O:55])=[CH:45][CH:44]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:23][C:24]1[S:28][C:27]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([CH2:38][C:39]([NH:42][C:43]4[CH:44]=[CH:45][C:46]([N:49]5[CH2:54][CH2:53][O:52][CH2:51][C:50]5=[O:55])=[CH:47][CH:48]=4)=[O:41])=[CH:37][C:31]=3[N:30]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 178525013[2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid

Product 1

HCID 178520191HCID 178520191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 139 mg (0.445 mmol) of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetra-methyluronium tetrafluoroborate (TBTU) are added to a solution of 100 mg (0.342 mmol) of [2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid and 65.7 mg (0.342 mmol) of 4-(4-aminophenyl)morpholin-3-one in 2 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 18 hours. Saturated aqueous sodium hydrogencarbonate solution is added to the reaction mixture, and the resultant precipitate is filtered off, washed with water and dried, giving 2-[2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]-N-[4-(3-oxomorpholin-4-yl)phenyl]acetamide as a brownish solid; ESI 467.

Workup

  1. filtrationthe resultant precipitate is filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ba1fee99328546659a91a6fb8f01aa6f
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Reaction notes

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