Sodium Bicarbonate → HCID 57670057, compound

HRID 1894478Notes

Reaction equation

HRID 1894478 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:41][CH2:42][CH3:43])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:50])=[O:49].C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([NH:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:41][CH2:42][CH3:43])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 57670001HCID 57670001, compound

Product 1

HCID 57670057HCID 57670057, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-one (64.6 mg, 0.104 mmole, example 209) and 2-aminoethyl methylsulfone hydrochloride (17.9 mg, 0.112 mmole, Array) in dichloromethane (3 mL) were added sodium acetate (21.1 mg, 0.257 mmole) and sodium triacetoxyborohydride (40.1 mg, 0.189 mmole). The mixture was stirred at room temperature overnight before saturated solution of sodium bicarbonate (3 mL) was added. After stirred for 1 h, the mixture was extracted with dichloromethane (2×10 mL). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, eluting with a gradient of 1% to 10% methanol in dichloromethane) to give the title compound (56.7 mg, 75% yield). HR-MS (ES, m/z) calculated for C37H48Cl2N5O4S [(M+H)+] 728.2799, observed 728.2796.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (2×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by flash column chromatography (silica gel
  7. washeluting with a gradient of 1% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b613d1607f434565a2fda2e77fff8d31
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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