Trifluoroacetic acid → HCID 178427171, compound

HRID 2053864Notes

Reaction equation

HRID 2053864 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[N:10]=[C:9]1[C@@H:18]([NH:24][C:25](=[O:40])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:33])=[C:28]([CH3:39])[CH:27]=1)[CH2:19][CH2:20][C:21]([OH:23])=O)=O)(C)(C)C.CN(C(O[N:49]1N=NC2C=[CH:53][CH:54]=[CH:55][C:50]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.N1CCCC1.FC(F)(F)C(O)=O.ClCl>O1CCCC1.C(OCC)(=O)C.C(O)C>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[NH:8][C:9]([C@@H:18]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:33])=[C:28]([CH3:39])[CH:27]=3)[CH2:19][CH2:20][C:21]([N:49]3[CH2:50][CH2:55][CH2:54][CH2:53]3)=[O:23])=[N:10][C:11]=2[CH:16]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69309945HCID 69309945, compound

Product 1

HCID 178427171HCID 178427171, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from (1S)—N-[1-(1-tert-butoxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, TBTU, diisopropylethylamine, and pyrrolidine in tetrahydrofuran followed by treatment with trifluoroacetic acid analogously to Example 17. Yield: 56%; Rf value: 0.22 (silica gel; ethyl acetate/ethanol=9:1); C28H32ClN5O3 (522.05); mass spectrum: (M+H)+=522/524 (chlorine isotope).

Sources & evidence

ORD record
ord-456fd7d6fec544be957fb3b389c46e19
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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