Acetic Anhydride → HCID 67389658, compound

HRID 1040572Notes

Reaction equation

HRID 1040572 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2([NH:14][C:15]([C:17]3([NH:20][C:21]([C:23]4[N:27]5[C@@:28]([CH2:41][C:42]6[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[CH:44][CH:43]=6)([CH3:40])[C:29](=[O:39])[N:30]([C:31]6[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=6)[C:26]5=[N:25][CH:24]=4)=[O:22])[CH2:19][CH2:18]3)=[O:16])[CH2:13][CH2:12]2)[CH:6]=1.[C:50](OC(=O)C)(=[O:52])[CH3:51]>C(Cl)Cl>[C:50]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2([NH:14][C:15]([C:17]3([NH:20][C:21]([C:23]4[N:27]5[C@@:28]([CH2:41][C:42]6[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[CH:44][CH:43]=6)([CH3:40])[C:29](=[O:39])[N:30]([C:31]6[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=6)[C:26]5=[N:25][CH:24]=4)=[O:22])[CH2:18][CH2:19]3)=[O:16])[CH2:12][CH2:13]2)[CH:6]=1)(=[O:52])[CH3:51]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86657596HCID 86657596, compound

Product 1

HCID 67389658HCID 67389658, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid {1-[1-(4-aminomethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-amide dihydrochloric acid salt (40 mg, 0.0539 mmol) was suspended in DCM (1 mL). TEA (0.038 mL, 0.269 mmol) was then added and the reaction mixture became homogeneous. Acetic anhydride (0.00624 mL, 0.0646 mmol) was then added. Stirred for 5 min. Solvent was evaporated. The resultant crude product was purified by reverse phase HPLC using 30-100% ACN/water as the gradient. Solvent was evaporated. The product was redissolved in 10% MeOH/DCM and filtered through a basic (NH2) cartridge. Solvent was evaporated to afford 24 mg of the title compound as a white solid, m/z 711.7 [M+1]+.

Workup

  1. customSolvent was evaporated
  2. customThe resultant crude product was purified by reverse phase
  3. customSolvent was evaporated
  4. dissolutionThe product was redissolved in 10% MeOH/DCM
  5. filtrationfiltered through a basic (NH2) cartridge
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-281f1e305ee14eaf9fc0a33007d31e19
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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