Water → HCID 57614313, compound

HRID 2273545Notes

Reaction equation

HRID 2273545 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[NH2:6][C:7]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[N:27]3[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]3)=[C:21]([NH:28][C:29](=[O:40])[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][CH2:38][OH:39])[CH:31]=3)[C:20]=2[CH3:41])=[O:18])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].O>N1C=CC=CC=1>[NH2:6][C:7]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[N:27]3[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]3)=[C:21]([NH:28][C:29](=[O:40])[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][CH2:38][O:39][S:1]([CH3:4])(=[O:3])=[O:2])[CH:31]=3)[C:20]=2[CH3:41])=[O:18])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 57500381HCID 57500381, compound

Product 1

HCID 57614313HCID 57614313, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

59 μl (0.77 mmol) of mesyl chloride are added to the solution of 0.34 g (0.69 mmol) of methyl 2-amino-5-[(1-{[3-(2-hydroxyethoxy)benzoyl]amino}-2-methylindolizin-3-yl)carbonyl]benzoate in 9 ml of pyridine at −20° C. under nitrogen. The reaction mixture is stirred for 2 hours at −20° C. and is then run into 100 ml of water. The precipitate obtained is filtered, washed thoroughly with water and dried under vacuum, to give 268 mg (70%) of a yellow powder.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered
  3. washwashed thoroughly with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d1a6b056e4af44deafedec4d2994c29c
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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