Hydrochloric Acid → Hydrochloric Acid

HRID 386686Notes

Reaction equation

HRID 386686 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([N:19]2[CH2:40][CH2:39][C:22]3([NH:26]/[C:25](=[N:27]/[C:28]([C:30]4[C:35]([NH2:36])=[N:34][C:33]([NH2:37])=[C:32]([Cl:38])[N:31]=4)=[O:29])/[NH:24][CH2:23]3)[CH2:21][CH2:20]2)=[O:18])=[CH:11][CH:10]=1)(C)(C)C.[ClH:42]>O1CCOCC1>[NH2:36][C:35]1[C:30]([C:28](/[N:27]=[C:25]2/[NH:26][C:22]3([CH2:39][CH2:40][N:19]([C:17](=[O:18])[CH2:16][CH2:15][C:12]4[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:41])=[O:5])=[CH:14][CH:13]=4)[CH2:20][CH2:21]3)[CH2:23][NH:24]/2)=[O:29])=[N:31][C:32]([Cl:38])=[C:33]([NH2:37])[N:34]=1.[ClH:42]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178451329[4-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidHCID 178508776[4-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

[4-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid tert-butyl ester (WO09074575, Ex. 71, page 134) (28.4 g, 48.4 mmol) was slurried in 1,4-dioxane (260 ml) and stirred for 1 h. 4N HCl in dioxane (121 ml, 484 mmol) was added dropwise over 15 min and the reaction mixture was stirred overnight. The resulting yellow solid was filtered and washed with diethyl ether. The solid was slurried in fresh diethyl ether (500 ml) and sonicated for 30 min. The resulting solid was collected by filtration and dried in vacuo to afford the title product as a mono hydrochloride, di-dioxan solvate; LC-MS Rt 0.79 rains; 531.3 and 533.3 [M+H]+, Method 2minLC_v003.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. filtrationThe resulting yellow solid was filtered
  3. washwashed with diethyl ether
  4. customsonicated for 30 min
  5. filtrationThe resulting solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-09186d8d501d4c41828426b3bb69c1b0
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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