Acetic Anhydride → HCID 178473827, compound

HRID 591956Notes

Reaction equation

HRID 591956 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C@@H:23]2[C@@H:28]3[CH2:29][C@@H:25]([CH:26]=[CH:27]3)[C@@H:24]2[C:30]([NH2:32])=[O:31])=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1>[C:33]([N:19]1[CH2:20][CH2:21][CH:16]([N:14]2[CH:15]=[C:11]([C:9]3[NH:8][C:5]4=[N:6][CH:7]=[C:2]([Cl:1])[C:3]([NH:22][C@@H:23]5[C@@H:28]6[CH2:29][C@@H:25]([CH:26]=[CH:27]6)[C@@H:24]5[C:30]([NH2:32])=[O:31])=[C:4]4[N:10]=3)[CH:12]=[N:13]2)[CH2:17][CH2:18]1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178514006HCID 178514006, compound

Product 1

HCID 178473827HCID 178473827, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(1S,2S,3R,4R)-3-[6-Chloro-2-(1-piperidin-4-yl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100 mg, 0.20 mmol) and acetic anhydride (45.1 mg, 0.442 mmol) were combined in pyridine (1 mL) and stirred at ambient temperature overnight. The mixture was concentrated and the crude product was purified employing reverse phase chromatography (Gilson) to afford following lyophilization of desired fractions a white lyophilate—the title compound (100%). 1H NMR (d-chloroform): 8.38 (d, J=8 Hz, 1H), 8.12 (s, 2H), 7.80 (s, 1H), 6.48 (m, 1H), 6.43 (m, 1H), 5.81 (br s, 1H), 5.40 (br s, 1H), 5.35 (m, 1H), 4.81 (m, 1H), 4.47 (m, 1H), 4.04 (m, 1H), 3.31 (t, J=8 Hz, 1H), 3.17 (s, 1H), 3.03 (s, 1H), 2.82 (m, 1H), 2.65 (m, 1H), 2.36-1.98 (m, 8H), 1.67 (d, J=8 Hz, 1H), 1.26 (d, J=8 Hz, 1H). MS: 494.9 (M+H). HPLC retention time: 1.88 minutes (G Method).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified
  3. customto afford

Sources & evidence

ORD record
ord-746128fd1e8f44dd832b3d3b95aec1d6
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…