Lithium Hydroxide → HCID 58724474, compound

HRID 1910156Notes

Reaction equation

HRID 1910156 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[N:16]=[C:15]([NH:18][C:19]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[CH2:27][NH:26][CH2:25][CH2:24]4)=[O:20])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8].CCN(C(C)C)C(C)C.Cl[C:41]([O:43][CH3:44])=[O:42].[Li+].[OH-]>CN(C=O)C.O>[CH3:44][O:43][C:41]([N:26]1[CH2:25][CH2:24][C:23]2[C:28](=[CH:29][CH:30]=[C:21]([C:19](=[O:20])[NH:18][C:15]3[NH:14][C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([C:7](=[O:8])[NH:6][C:2]5[NH:1][CH:5]=[CH:4][N:3]=5)[C:17]=4[N:16]=3)[CH:22]=2)[CH2:27]1)=[O:42]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 58724484HCID 58724484, compound

Product 1

HCID 58724474HCID 58724474, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

41 mg (0.08 mmol) of 1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide in 0.6 mL of DMF and 0.176 mL (1 mmol) of DIEA was treated with 0.024 mL (0.3 mmol) of methyl chloroformate and stirred at room temperature for 14 h. The reaction mixture was then treated with 0.15 mL of 2 N aq. LiOH. Water was added to the reaction mixture. The precipitated solid was collected by filtration and washed with water to yield 11.4 mg (0.0248 mmol, 31%) of 6-[4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-ylcarbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester. LCMS: 460 (M+1)+.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-29d78becac7e4fd49c8c0f43399c9cd9
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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