Dimethylamine → HCID 23537798, compound

HRID 1792595Notes

Reaction equation

HRID 1792595 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]2[CH:11]=[C:12]([C:15]3[C:16]([C:39]4[S:43]C(C(O)=O)=CC=4)=[N:17][N:18]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1.[CH2:47]([N:49](CC)[CH2:50]C)C.ClC(OCC(C)C)=O.CNC.[O:65]1[CH2:69][CH2:68][CH2:67][CH2:66]1>O>[CH3:47][N:49]([CH3:50])[C:66]([C:67]1[S:43][C:39]([C:16]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]4[N:10]([C:6]([C:2]5[S:1][CH:5]=[CH:4][N:3]=5)=[CH:7][N:8]=4)[CH:11]=3)=[CH:19][N:18]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:17]=2)=[CH:69][CH:68]=1)=[O:65]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22031054HCID 22031054, compound

Product 1

HCID 23537798HCID 23537798, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg 5-{4-[3-(1,3-thiazol-2-yl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}-2-thiophene carboxylic acid (compound in Example 443), together with 66 μL triethylamine and 25 μL isobutyl chloroformate, was stirred for 30 minutes in 4 mL tetrahydrofuran under ice-cooling in a stream of nitrogen, and then 0.79 mL dimethylamine was added thereto and stirred at room temperature for 3 hours. Water was added to the reaction solution which was then extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 29 mg of the title compound (colorless solid).

Workup

  1. temperaturecooling in a stream of nitrogen
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7f5fc539321f45eca307cded64465912
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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