Diisopropylethylamine → HCID 57407263, compound

HRID 925596Notes

Reaction equation

HRID 925596 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:25]5[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=5)[N:19]=[C:20](S(C)(=O)=O)[C:15]4=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:32]([O:36][C:37](=[O:43])[NH:38][CH2:39][CH2:40][CH2:41][NH2:42])([CH3:35])([CH3:34])[CH3:33].CCN(C(C)C)C(C)C>>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:25]5[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=5)[N:19]=[C:20]([NH:42][CH2:41][CH2:40][CH2:39][NH:38][C:37](=[O:43])[O:36][C:32]([CH3:34])([CH3:33])[CH3:35])[C:15]4=[N:14][CH:13]=3)=[CH:8][CH:7]=2)=[O:31])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 67973144HCID 67973144, compound

Product 1

HCID 57407263HCID 57407263, compoundYield 16.9%

Conditions

Temperature
170 °C

Procedure

0.1 mmol N-cyclopropyl-4-[8-(methylsulfonyl)-6-(pyridin-4-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide (intermediate example 9-2) (1 mL, 0.1 M in NMP), 0.2 mmol tert-butyl(3-aminopropyl)carbamate (0.4 mL, 0.5 M in NMP, 2 eq) and 0.3 mmol DIPEA (41 μL, 3 eq) were combined in a sealed vial and heated at 170° C. under microwave irradiation for 60 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 8.9 mg tert-butyl [3-({3-[4-(cyclopropylcarbamoyl)phenyl]-6-(pyridin-4-yl)imidazo[1,2-a]pyrazin-8-yl}amino)propyl]carbamate (11%): 1H-NMR (300 MHz, d6-DMSO): δ=8.58 (2H, d), 8.54 (1H, d), 8.32 (1H, s), 8.02-7.93 (3H, m), 7.87-7.76 (4H, m), 6.83 (1H, tr), 3.58 (2H, m), 3.01 (2H, m), 2.86 (1H, m), 1.77 (2H, m), 1.32 (9H, s), 0.68 (2H, m), 0.55 (2H, m) ppm; UPLC-MS: RT=0.90 min; m/z (ES+) 528.6 [MH+]; required MW=527.6.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-d1db2c04d9cf4d828e3247478a6c12ba
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

Loading…