1,4-Dioxane → HCID 178508766, compound

HRID 386698Notes

Reaction equation

HRID 386698 reaction equation
C([O:5][C:6]([C:8]1([CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([N:25]3[CH2:46][CH2:45][C:28]4([NH:32]/[C:31](=[N:33]/[C:34]([C:36]5[C:41]([NH2:42])=[N:40][C:39]([NH2:43])=[C:38]([Cl:44])[N:37]=5)=[O:35])/[NH:30][CH2:29]4)[CH2:27][CH2:26]3)=[O:24])[CH:18]=2)(=[O:16])=[O:15])[CH2:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.O1CCOCC1>Cl>[NH2:42][C:41]1[C:36]([C:34](/[N:33]=[C:31]2/[NH:32][C:28]3([CH2:45][CH2:46][N:25]([C:23]([C:19]4[CH:18]=[C:17]([S:14]([NH:13][CH2:12][C:8]5([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][CH2:11]5)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=4)=[O:24])[CH2:26][CH2:27]3)[CH2:29][NH:30]/2)=[O:35])=[N:37][C:38]([Cl:44])=[C:39]([NH2:43])[N:40]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 178450772HCID 178450772, compound

Product 1

HCID 178508766HCID 178508766, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 1-[(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid tert-butyl ester (step 1) (730 mg, 1.080 mmol) in 4N HCl in dioxane (10 ml, 40.0 mmol) was stirred at RT for 1 h. The reaction mixture was partitioned between water and EtOAc and the pH of the aqueous portion was adjusted to 14 by addition of 2N NaOH. The basic aqueous solution was washed with EtOAc and concentrated in vacuo. The dry residue was slurried in water and the pH was adjusted to 6 by dropwise addition of 2N HCl. The resulting solid was filtered and washed with water (20 ml), diethyl ether (20 ml) and dried under vacuum at 50° C. to afford the title product; LC-MS Rt 2.29 mins; 620.3 [M+H]+, Method 10minLC_v003.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. additionthe pH of the aqueous portion was adjusted to 14 by addition of 2N NaOH
  3. washThe basic aqueous solution was washed with EtOAc
  4. concentrationconcentrated in vacuo
  5. additionthe pH was adjusted to 6 by dropwise addition of 2N HCl
  6. filtrationThe resulting solid was filtered
  7. washwashed with water (20 ml), diethyl ether (20 ml)
  8. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-50060ee2c80f44029583f5532634199d
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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