Water → HCID 16117743, compound

HRID 2039723Notes

Reaction equation

HRID 2039723 reaction equation
Cl.[N:2]1[C:7]2[NH:8][CH:9]=[C:10]([C:11]3[N:16]=[C:15]([C:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=4)[CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[N:4][CH:3]=1.[C:23]([CH2:25][C:26](ON1CCCC1)=[O:27])#[N:24].C(N(C(C)C)CC)(C)C.O>C(O)C>[O:27]=[C:26]([N:20]1[CH2:19][CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]3[C:6]4[CH:5]=[N:4][CH:3]=[N:2][C:7]=4[NH:8][CH:9]=3)[N:16]=2)[CH2:22][CH2:21]1)[CH2:25][C:23]#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 570164291-Pyrrolidinyl 2-cyanoacetateHCID 69513664HCID 69513664, compound

Product 1

HCID 16117743HCID 16117743, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As shown in FIG. 7—step v, compound 29 (30 mg) and 2-cyano acetic acid, pyrrolidin-1-yl ester (47 mg) were mixed in ethanol (2 mL) and diisopropylethylamine (0.084 mL) was added. After stirring at rt for 12 hours, water (30 mL) was added. Extraction with dichloromethane (3×) and chromatographic purification (SiO2, ethyl acetate) afforded 5.3 mg of 3-oxo-3-[6-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-yl]-propionitrile (compound 30).

Workup

  1. extractionExtraction
  2. customwith dichloromethane (3×) and chromatographic purification (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-01b70f409264402c960c2992d08ef95a
Source dataset
uspto-grants-2013_11
Patent number
US08580802B2

Reaction notes

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