Hydrochloric Acid → HCID 90414946, compound

HRID 1526660Notes

Reaction equation

HRID 1526660 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:10]=[N:11][C:12]([C:15](=[O:35])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C@:24]3([CH:32]([F:34])[F:33])[C@@H:30]4[C@@H:28]([CH2:29]4)[O:27][C:26]([NH2:31])=[N:25]3)[CH:18]=2)=[N:13][CH:14]=1)C)(C)(C)C.[ClH:37].O>O1CCOCC1>[ClH:37].[ClH:37].[NH2:31][C:26]1[O:27][C@H:28]2[C@@H:30]([C@:24]([C:19]3[CH:18]=[C:17]([NH:16][C:15]([C:12]4[N:13]=[CH:14][C:9]([NH:7][CH3:6])=[CH:10][N:11]=4)=[O:35])[CH:22]=[CH:21][C:20]=3[F:23])([CH:32]([F:34])[F:33])[N:25]=1)[CH2:29]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 118232921HCID 118232921, compound

Product 1

HCID 90414946HCID 90414946, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl(2-((3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)carbamoyl)pyrimidin-5-yl)(methyl)carbamate (0.06 g, 0.11 mmol) in 1,4-dioxane (2 mL) was treated with HCl (4.0M in 1,4-dioxane; 1 mL). The resulting suspension was treated with water (0.1 mL) resulting in a pale-yellow biphasic solution. The solution was stirred for 2 h, concentrated, and lyophilized from 1,4-dioxane to give N-(3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-(methylamino)pyrimidine-2-carboxamide dihydrochloride (0.05 g, 0.105 mmol, 93% yield) as a pale-yellow solid.

Workup

  1. customresulting in a pale-yellow biphasic solution
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-520e484d65e94023a0bc5de73841d687
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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