Sodium Bicarbonate → HCID 86626794, compound

HRID 604034Notes

Reaction equation

HRID 604034 reaction equation
[F:1][C:2]([F:58])([F:57])[C:3]1[CH:4]=[C:5]([CH:50]=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:52]=1)[CH2:6][N:7]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=1[N:31]([CH2:43][CH2:44][O:45][C:46](C)(C)[CH3:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:8]1[N:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][N:9]=1.C(=O)(O)[O-:60].[Na+]>Cl.C(OCC)(=O)C>[C:46]([O:45][CH2:44][CH2:43][N:31]([C:22]1[CH:23]=[CH:24][C:25]([C:27]([F:29])([F:30])[F:28])=[CH:26][C:21]=1[CH2:20][N:7]([CH2:6][C:5]1[CH:50]=[C:51]([C:53]([F:55])([F:54])[F:56])[CH:52]=[C:3]([C:2]([F:58])([F:1])[F:57])[CH:4]=1)[C:8]1[N:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][N:13]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(=[O:60])[CH3:47]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86626795HCID 86626795, compound

Product 1

HCID 86626794HCID 86626794, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl 7-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-(2-tert-butoxy-ethyl)-amino]-heptanoate (which is prepared by treating the corresponding starting compound in a same manner as in Example 12(1)-(4)) (260 mg) is dissolved in a 4N-hydrochloric acid in ethyl acetate (4 ml) and the mixture is stirred at room temperature overnight. To the reaction solution are added a saturated aqueous sodium bicarbonate solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2) to give ethyl 7-[(2-acetoxy-ethyl)-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-amino]-heptanoate (162 mg). MS (m/z): 822 [M+H]+

Workup

  1. additionby treating the
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

Sources & evidence

ORD record
ord-8856e77adbe74d718bd9046e72abd309
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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