Acetic Anhydride → HCID 178491978, compound

HRID 591951Notes

Reaction equation

HRID 591951 reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C@@H:27]2[C@@H:32]3[CH2:33][C@@H:29]([CH:30]=[CH:31]3)[C@@H:28]2[C:34]([NH2:36])=[O:35])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:13][C:12]=3[O:24][CH3:25])[NH:8][C:5]2=[N:6][CH:7]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38].C(N(CC)CC)C>ClCCl>[C:37]([N:21]1[CH2:22][CH2:23][N:18]([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:9]3[NH:8][C:5]4=[N:6][CH:7]=[C:2]([Cl:1])[C:3]([NH:26][C@@H:27]5[C@H:32]6[CH2:33][C@@H:29]([CH:30]=[CH:31]6)[C@@H:28]5[C:34]([NH2:36])=[O:35])=[C:4]4[N:10]=3)=[C:12]([O:24][CH3:25])[CH:13]=2)[CH2:19][CH2:20]1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178491965HCID 178491965, compound

Product 1

HCID 178491978HCID 178491978, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S,2S,3R,4R)-3-[6-Chloro-2-(2-methoxy-4-piperazin-1-ylmethyl-phenyl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (Compound XLII) (254 mg, 0.5 mmol) was dissolved in anhydrous dichloromethane (10 mL) and treated with acetic anhydride (1 mL, 10.0 mmol) and triethylamine (1.0 mL, 7.2 mmol) for one hour at ambient temperature. The reaction was concentrated and the product was purified by reverse phase chromatography (Gilson) to afford following neutralization of desired fractions a pale yellow solid as the title compound (91 mg, 30%). Mp 109-113° C. 1H NMR (d-chloroform): 11.12 (br s, 1H), 8.34 (d, J=7 Hz, 1H), 7.99 (s, 1H), 7.11 (m, 2H), 6.37 (m, 3H), 5.72 (d, J=7 Hz, 1H), 5.36 (m, 1H), 5.22 (t, J=8 Hz, 1H), 4.10 (s, 3H), 3.66 (m, 2H), 3.59 (s, 2H), 3.50 (m, 2H), 3.17 (s 1H), 2.92 (s, 1H), 2.85 (d, J=7 Hz, 1H), 2.48 (m, 4H), 2.34 (d, J=8 Hz, 1H), 2.10 (s, 3H), 1.73 (d, J=7 Hz, 1H). MS: 550.2 (M+H). HPLC retention time: 1.70 minutes (G Method).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe product was purified by reverse phase chromatography (Gilson)
  3. customto afford

Sources & evidence

ORD record
ord-f3afb3d2017f45f6b0ce3f59b17284d0
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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