Methylamine → HCID 178485717, compound

HRID 2054035Notes

Reaction equation

HRID 2054035 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1C(N1CCC[C@@H]1CC(O)=O)=O)[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6].[CH3:34][N:35]([C:37]([O:41]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([N:59]([CH:62]([CH3:64])[CH3:63])[CH2:60][CH3:61])(C)C.CN.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[N:59]1[CH2:60][CH2:61][CH2:64][C@@H:62]1[CH2:63][C:37]([NH:35][CH3:34])=[O:41])[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178462066HCID 178462066, compound

Product 1

HCID 178485717HCID 178485717, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-[(2R)-2-(hydroxycarbonylmethyl)pyrrolidin-1-ylcarbonyl]benzamide, TBTU, diisopropylethylamine, and methylamine in tetrahydrofuran. Yield: 60%; Rf value: 0.44 (silica gel: dichloromethane/ethanol=9:1); C24H25Cl2N5O3 (502.405); mass spectrum: (M+H)+=502/504/506 (chlorine isotope) and (M−H)−=500/502/504 (chlorine isotope).

Sources & evidence

ORD record
ord-b50cc0c41d2241f480ebddbc2eedaebf
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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