Acetyl chloride → HCID 178474743, compound

HRID 2053845Notes

Reaction equation

HRID 2053845 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:17][C:18](=[O:33])[C:19]1[CH:24]=[CH:23][C:22]([C:25]([N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])=[C:21]([CH3:32])[CH:20]=1)[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:9]=2[N:8]=1.[C:34](Cl)(=[O:36])[CH3:35].C(N(CC)CC)C.ClCl>O1CCCC1.ClCCl.CO>[C:34]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:17][C:18](=[O:33])[C:19]1[CH:24]=[CH:23][C:22]([C:25]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:26])=[C:21]([CH3:32])[CH:20]=1)[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:9]=2[N:8]=1)(=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 24526ChlorineHCID 178427160HCID 178427160, compound

Product 1

HCID 178474743HCID 178474743, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 23a from N-[(1S)-5-amino-1-(5-chloro-1H-benzimidazol-2-yl)pentyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, acetyl chloride, and triethylamine in tetrahydrofuran. Yield: 55%; Rf value: 0.2 (silica gel; dichloromethane/methanol=9:1); C27H32ClN5O3 (510.04); mass spectrum: (M−H)−=510/512 (chlorine isotope).

Sources & evidence

ORD record
ord-73321c7a0fa94f32a2965de1994ad0bf
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…