Potassium Iodide → {[(cyclohexyloxy)carbonyl]oxy}methyl (2R)-3-[1-amino-7-(trifluoromethoxy)isoquinolin-6-yl]-2-[(3S)-2-oxo-3-({[2-(pyrrolidin-1-yl)-1,3-thiazol-5-yl]sulfonyl}amino)pyrrolidin-1-yl]propanoate

HRID 1746848Notes

Reaction equation

HRID 1746848 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:18][C@@H:19]([N:23]3[CH2:27][CH2:26][C@H:25]([NH:28][S:29]([C:32]4[S:36][C:35]([N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)=[N:34][CH:33]=4)(=[O:31])=[O:30])[C:24]3=[O:42])[C:20]([OH:22])=[O:21])=[C:10]([O:13][C:14]([F:17])([F:16])[F:15])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:49](=[O:60])([O:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1)[O:50][CH2:51]Cl.[I-].[K+]>CN(C=O)C.O>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:18][C@@H:19]([N:23]3[CH2:27][CH2:26][C@H:25]([NH:28][S:29]([C:32]4[S:36][C:35]([N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)=[N:34][CH:33]=4)(=[O:31])=[O:30])[C:24]3=[O:42])[C:20]([O:22][CH2:51][O:50][C:49]([O:53][CH:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]3)=[O:60])=[O:21])=[C:10]([O:13][C:14]([F:15])([F:17])[F:16])[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13603586Chloromethyl cyclohexyl carbonateHCID 71584487(R)-3-(1-Amino-7-trifluoromethoxy-isoquinolin-6-yl)-2-[(S)-2-oxo-3-(2-pyrrolidin-1-yl-thiazole-5-sulfonylamino)-pyrrolidin-1-yl]-propionic acid hydrochloride2×

Product 1

HCID 89644321{[(cyclohexyloxy)carbonyl]oxy}methyl (2R)-3-[1-amino-7-(trifluoromethoxy)isoquinolin-6-yl]-2-[(3S)-2-oxo-3-({[2-(pyrrolidin-1-yl)-1,3-thiazol-5-yl]sulfonyl}amino)pyrrolidin-1-yl]propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-3-[1-amino-7-(trifluoromethoxy)isoquinolin-6-yl]-2-[(3S)-2-oxo-3-({[2-(pyrrolidin-1-yl)-1,3-thiazol-5-yl]sulfonyl}amino)pyrrolidin-1-yl]propanoic acid hydrochloride (compound of example 4) (0.5 g, 0.73 mmol) in anhydrous DMF (3 ml) were added potassium carbonate (0.3 g, 2.2 mmol) and chloromethyl cyclohexyl carbonate (0.21 g, 1.1 mmol), followed by potassium iodide (12 mg, 0.07 mmol). The reaction mixture was stirred at room temperature under nitrogen for 12 hours, and then was poured onto cold water, the resulting precipitate was filtered of, washed with water and dried under P2O5.

Workup

  1. filtrationthe resulting precipitate was filtered of,
  2. washwashed with water
  3. customdried under P2O5

Sources & evidence

ORD record
ord-dbf50bf2425e4fb193a2b250ee81a6fe
Source dataset
uspto-grants-2015_10
Patent number
US09150544B2

Reaction notes

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