Trifluoroacetic acid → 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-(2-aminomethylpyrrolidin-1-ylcarbonyl)benzamide

HRID 2053882Notes

Reaction equation

HRID 2053882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:22]([OH:24])=O)[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6].CN(C(O[N:33]1N=[N:40][C:35]2[CH:36]=[CH:37][CH:38]=C[C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(OC(NCC1CCCN1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCl>CN(C=O)C>[NH2:33][CH2:34][CH:35]1[CH2:36][CH2:37][CH2:38][N:40]1[C:22]([C:21]1[CH:20]=[CH:19][C:4]([C:5]([NH:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=3[N:10]=2)=[O:6])=[CH:3][C:2]=1[Cl:1])=[O:24]

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21834643Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl esterHCID 178523088HCID 178523088, compound

Product 1

HCID 1785099733-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-(2-aminomethylpyrrolidin-1-ylcarbonyl)benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-carboxybenzamide, TBTU, diisopropylethylamine, and rac.-2-tert-butoxycarbonylaminomethylpyrrolidine in DMF followed by treatment with trifluoroacetic acid analogously to Example 17. Yield: 47%; C21H21Cl2N5O2 (446.34); mass spectrum: (M+H)+=446/448/450 (chlorine isotope).

Sources & evidence

ORD record
ord-fe9fe5d0310040589d6edb0115c58771
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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