Diisopropylethylamine → HCID 25152047, compound

HRID 2066822Notes

Reaction equation

HRID 2066822 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C:11]([CH2:14][NH:15][C:16](=[O:37])[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:24][C:25]5[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([C:35]#[N:36])=[CH:28][C:26]=5[N:27]=4)=[CH:19][CH:18]=3)([CH3:13])[O:10][C:9]2=[O:38])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[N:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[C:54](Cl)=[O:55]>ClCCl>[C:35]([C:29]1[CH:30]=[C:31]([CH:32]([CH3:34])[CH3:33])[C:25]2[O:24][C:23]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([NH:15][CH2:14][C:11]4([CH3:13])[O:10][C:9](=[O:38])[N:8]([C:5]5[N:6]=[CH:7][C:2]([NH:1][C:54]([C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][N:48]=6)=[O:55])=[CH:3][CH:4]=5)[CH2:12]4)=[O:37])=[CH:22][CH:21]=3)=[N:27][C:26]=2[CH:28]=1)#[N:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 68409139HCID 68409139, compound2×

Product 1

HCID 25152047HCID 25152047, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{[3-(5-aminopyridin-2-yl)-5-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (10 mg, INTERMEDIATE 23) and diisopropylethylamine (7 μl) in 4 ml of dichloromethane was added picolinoyl chloride (3 mg). The mixture was stirred at room temperature for 1 h. The sample was purified directly via column chromatography on a Biotage Horizon 12M column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 4 column volumes to provide the title compound (4 mg, 34%). Mass spectrum (ESI) 616.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 9.01 (s, 1H), 8.69 (d, J=3.9 Hz, 1H), 8.47 (d, J=8.4 Hz, 2H), 8.33 (d, J=8.3 Hz, 2H), 8.31 (d, J=7.8 Hz, 1H), 8.16 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.92 (s, 1H), 7.73 (s, 1H), 7.51 (s, 1H), 7.41 (bs, 1H), 6.65 (bs, 1H), 4.94 (bs, 1H), 4.04 (d, J=10.3 Hz, 1H), 3.99 (dd, J=14.2, 6.6 Hz, 1H), 3.83 (dd, J=14.4, 6.4 Hz, 1H), 3.47 (sept, J=7.0 Hz, 1H), 1.67 (s, 3H), 1.46 (d, J=6.9 Hz, 6H).

Workup

  1. customThe sample was purified directly via column chromatography on a Biotage Horizon 12M column
  2. washeluting with 0% ethyl acetate in hexanes (1 column volume)

Sources & evidence

ORD record
ord-23ebeb50aac44921b88cef17ef923dc9
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

Loading…