Hydrochloric Acid → Hydrochloric Acid

HRID 2170082Notes

Reaction equation

HRID 2170082 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-4553652e233c409d808a00277614828c
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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