Diisopropylethylamine → HCID 68662423, compound

HRID 2388977Notes

Reaction equation

HRID 2388977 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=4)=[N:15][N:14]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:33](=[O:37])[N:34]([CH3:36])[CH3:35].[N:38]1([C:44](Cl)=[O:45])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:44]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[O:45])=[C:3]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[CH:4]=3)[CH:9]=2)[N:14]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:30])[CH3:31])[N:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 68662574HCID 68662574, compound

Product 1

HCID 68662423HCID 68662423, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

2,2-Dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(3-chloro-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (300 mg, 0.577 mmol), chloroform (50 ml), 4-morpholinecarbonyl chloride (1.2 ml, 10.45 mmol), and di-iso-propyl ethyl amine (2.4 ml, 13.78 mmol) were combined and stirred for 48 hours at 50° C. The reaction was quenched with sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes) to give 180 mg (49%) of 2,2-dimethyl-propionic acid 3-(3-chloro-benzyl)-5-{3-dimethylcarbamoyl-4-[(morpholine-4-carbonyl)-amino]-phenyl}-pyrazolo[3,4-b]pyridin-1-ylmethyl ester. MS: m/z 633.5 (M+H+).

Workup

  1. customThe reaction was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes)

Sources & evidence

ORD record
ord-8321dadd5c87463f8d14b1faa009def7
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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