Diisopropylethylamine → HCID 58653632, compound

HRID 1676039Notes

Reaction equation

HRID 1676039 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]([OH:29])=O)[CH2:23][CH2:22]3)[C:15]=2[N:14]=[CH:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Br.[NH2:63][C:64]1[NH:65][CH2:66][CH2:67][CH2:68][N:69]=1>CN(C=O)C>[C:6]1([CH:5]([N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([N:21]4[CH2:22][CH2:23][CH:24]([C:27]([NH:63][C:64]5[NH:69][CH2:68][CH2:67][CH2:66][N:65]=5)=[O:29])[CH2:25][CH2:26]4)[C:15]=3[N:14]=[CH:13]2)[CH2:4][C:3]([O:2][CH3:1])=[O:30])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58653705HCID 58653705, compoundHCID 67352751HCID 67352751, compound

Product 1

HCID 58653632HCID 58653632, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[1-(3-methoxy-3-oxo-1-phenylpropyl)-1H-benzimidazol-4-yl]-4-piperidinecarboxylic acid (70 mg, 172 μmol) in DMF was added N,N-diisopropylethylamine (60 μL, 344 μmol) and TBTU (66 mg, 206 μmol). The solution was stirred at room temperature for 0.5 hour, then 2-amino-1,4,5,6-tetrahydropyrimidine hydrobromide (34 mg, 189 μmol) was added. The mixture was heated to 80° C. for 8 hours, cooled to room temperature, and evaporated in vacuo. The residue was purified by RP-HPLC to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=4.66 min, MH+ 489].

Workup

  1. temperatureThe mixture was heated to 80° C. for 8 hours
  2. temperaturecooled to room temperature
  3. customevaporated in vacuo
  4. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-7d5f0918f4664e5abdf11c589456f3ec
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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