Ammonia → HCID 10360132, compound

HRID 751302Notes

Reaction equation

HRID 751302 reaction equation
[NH3:1].C([O:4][C:5]([C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:19][N:18]4[CH2:27][CH2:28][CH2:29][C:17]=34)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1)=O)C.ClCCl.CO>CO>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]1[C:16]([C:13]2[CH:14]=[CH:15][C:10]3[N:11]([C:7]([C:5]([NH2:1])=[O:4])=[CH:8][N:9]=3)[CH:12]=2)=[C:17]2[CH2:29][CH2:28][CH2:27][N:18]2[N:19]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226129Dichloromethane methanolHCID 58611951HCID 58611951, compound

Product 1

HCID 10360132HCID 10360132, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

Add 7N ammonia in methanol (10 mL) to a sealed tube containing 6-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (Example 35; 0.105 g, 0.28 mmol). Heat at 110° C. for 48 h. Flash chromatograph using dichloromethane/methanol mixtures to give the title compound (0.08 g, 82%) as a white solid. MS ES+ m/e 344.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 8.4-8.37 (m, 1H), 8.28 (s, 1H), 7.82-7.77 (m, 3H), 7.59 (d, J=9 Hz, 1H), 7.4 (dd, J=9.0, 2.0 Hz, 1H), 7.25 (m, 1H), 4.21 (t, J=7 Hz, 2H), 2.99 (t, J=7, 2H), 2.62 (quintet, 2H, 8 Hz).

Sources & evidence

ORD record
ord-d6cbae1e89764f429e45259c97b4e492
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

Loading…