Lithium Hydroxide → HCID 58724474, compound

HRID 1367885Notes

Reaction equation

HRID 1367885 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-5fc7cf48a294432f800b3548275dafea
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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