Ethanolamine → HCID 24810384, compound

HRID 2081114Notes

Reaction equation

HRID 2081114 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C([O:7][C:8]([C:10]1[C:11]2[S:19][CH:18]=[C:17]([CH2:20][O:21][C:22]3[CH:27]=[C:26]([C:28]4[N:32]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=5)[C:31]([CH3:42])=[N:30][N:29]=4)[CH:25]=[CH:24][C:23]=3[CH3:43])[C:12]=2[C:13]([NH2:16])=[N:14][CH:15]=1)=O)C>CS(C)=O.O>[OH:2][CH2:1][CH2:3][NH:4][C:8]([C:10]1[C:11]2[S:19][CH:18]=[C:17]([CH2:20][O:21][C:22]3[CH:27]=[C:26]([C:28]4[N:32]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=5)[C:31]([CH3:42])=[N:30][N:29]=4)[CH:25]=[CH:24][C:23]=3[CH3:43])[C:12]=2[C:13]([NH2:16])=[N:14][CH:15]=1)=[O:7]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 24810340HCID 24810340, compound

Product 1

HCID 24810384HCID 24810384, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

Ethanolamine (1.8 mL; 29.9 mmol) (Aldrich) was added to a solution of 4-amino-3-{5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (50 mg; 0.08277 mmole) (from Example 59 supra) in dimethylsulfoxide (0.6 mL). The mixture was heated in a microwave reactor at 135° C. for 2.25 hours. After cooling to room temperature, the reaction mixture was diluted with water, resulting in precipitation of the product as a milky solid which was collected by centrifugation and dried. The crude solid was triturated with hot methanol, cooled slightly, filtered and dried, to give 4-amino-3-{5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide in two crops. (Yield 31.2 mg, 51.3%). HRMS (ES+) m/z Calcd for C29H30N6O4S+H [(M+H)+]: 559.2122. Found: 559.2120.

Workup

  1. temperatureAfter cooling to room temperature
  2. customresulting in precipitation of the product as a milky solid which
  3. customwas collected by centrifugation
  4. customdried
  5. customThe crude solid was triturated with hot methanol
  6. temperaturecooled slightly
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-28c7745a130e41dd9f0f60ef92c70669
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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