Ammonia → HCID 178462089, compound

HRID 551187Notes

Reaction equation

HRID 551187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])[C:5]([OH:7])=O.[Cl:18][C:19]1[CH:30]=[CH:29][C:22]2[NH:23][C:24]([C@@H:26]([NH2:28])[CH3:27])=[N:25][C:21]=2[CH:20]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.N>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])[C:5]([NH:28][C@H:26]([C:24]1[NH:23][C:22]2[CH:29]=[CH:30][C:19]([Cl:18])=[CH:20][C:21]=2[N:25]=1)[CH3:27])=[O:7]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 643195303-Chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzoic acid

Product 1

HCID 178462089HCID 178462089, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1f from 3-chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzoic acid, (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine, TBTU and NMM in DMF, then pouring into ice water, adding conc. ammonia solution, filtering, washing with water and purifying by chromatography on silica gel (eluting gradient ethyl acetate/(methanol/conc. ammonia solution 19:1)=98:2→90:10) with subsequent filtration through activated charcoal, trituration with ether and drying in the drying pistol at 70° C.

Workup

  1. filtrationfiltering
  2. washwashing with water
  3. filtrationpurifying by chromatography on silica gel (eluting gradient ethyl acetate/(methanol/conc. ammonia solution 19:1)=98:2→90:10) with subsequent filtration through activated charcoal, trituration with ether
  4. customdrying in the drying pistol at 70° C.

Sources & evidence

ORD record
ord-40655efe7ae04ccfbd2e3514e3ae49aa
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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