Chlorine → HCID 178427169, compound

HRID 2053868Notes

Reaction equation

HRID 2053868 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:49]([O:53][C:54]([NH:56][CH2:57][CH2:58][CH2:59][C@H:60]([NH2:71])[C:61]1[NH:65][C:64]2[CH:66]=[CH:67][C:68]([Cl:70])=[CH:69][C:63]=2[N:62]=1)=[O:55])([CH3:52])([CH3:51])[CH3:50].ClCCl.CO.N.ClCl>O1CCCC1>[C:49]([O:53][C:54]([NH:56][CH2:57][CH2:58][CH2:59][C@H:60]([NH:71][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[C:61]1[NH:65][C:64]2[CH:66]=[CH:67][C:68]([Cl:70])=[CH:69][C:63]=2[N:62]=1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

8

Reactant 6

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 21584172Ammonia methanol dichloromethaneHCID 178453439HCID 178453439, compound

Product 1

HCID 178427169HCID 178427169, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (S)-4-(tert-butoxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)butylamine in tetrahydrofuran. Yield: 82%; Rf value: 0.60 (silica gel; dichloromethane/methanol/ammonia=95:5:0.1); C29H36ClN5O4 (554.09); mass spectrum: (M+H)+=554/556 (chlorine isotope).

Sources & evidence

ORD record
ord-cb25c17ca5c44aac8c998b9a2adb2017
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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