2-Morpholinoethanol → {2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic acid 2-morpholin-4-yl-ethyl Ester

HRID 2234641Notes

Reaction equation

HRID 2234641 reaction equation
[F:1][C:2]1[C:3]([N:40]=[C:41]=[O:42])=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][N:19]([S:30]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[OH:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C(N(CC)C(C)C)(C)C>ClCCl>[N:46]1([CH2:45][CH2:44][O:43][C:41](=[O:42])[NH:40][C:3]2[C:2]([F:1])=[CH:12][C:11]([C:13]3[CH:14]=[C:15]4[C:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[O:28][CH3:29])=[CH:20][N:19]([S:30]([C:33]5[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=5)(=[O:32])=[O:31])[C:16]4=[N:17][CH:18]=3)=[CH:10][C:4]=2[C:5](=[O:6])[N:7]([CH3:9])[CH3:8])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 611632-Morpholinoethanol2×HCID 81531DiisopropylethylamineHCID 577314603-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Product 1

HCID 57731435{2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic acid 2-morpholin-4-yl-ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

75 mg (0.13 mmol) of 3-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 1.0 mL dichloromethane and combined with 31 μL (0.26 mmol) of 4-(2-hydroxyethyl)-morpholine (which was dried over molecular sieves) and 22 μL (0.13 mmol) of N,N-diisopropylethylamine. The reaction was stirred for 16 hours at room temperature. 31 μL (0.26 mmol) of 4-(2-hydroxyethyl)morpholine was added and the reaction was continued to stir for 24 hours at room temperature. The reaction was concentrated and purified by flash chromatography on silica gel using a gradient of ethyl acetate (containing 10% methanol) and hexanes. The clean fractions were concentrated. MS: m/z 715.3 (M+H+).

Workup

  1. stirringto stir for 24 hours at room temperature
  2. concentrationThe reaction was concentrated
  3. custompurified by flash chromatography on silica gel using a gradient of ethyl acetate (containing 10% methanol) and hexanes
  4. concentrationThe clean fractions were concentrated

Sources & evidence

ORD record
ord-0df861e7978a45c3918a7ff1fd8e9a51
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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