Dichloromethane → HCID 67111738, compound

HRID 1177616Notes

Reaction equation

HRID 1177616 reaction equation
[Cl-].[Ca+2].[Cl-].[C:4]([NH:7][C:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]3[C:33]([N:34]=2)=[CH:32][CH:31]=[C:30]([C:35]2([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:37][CH2:36]2)[N:29]=3)=[C:22]([F:44])[CH:21]=1)([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])(=[O:6])[CH3:5].[BH4-].[Na+].C(Cl)Cl>O.C1COCC1.C(O)C>[F:44][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[C:26]1[S:27][C:28]2[C:33]([N:34]=1)=[CH:32][CH:31]=[C:30]([C:35]1([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:37][CH2:36]1)[N:29]=2)[CH2:19][C:8]([NH:7][C:4](=[O:6])[CH3:5])([CH2:14][OH:15])[CH2:9][OH:10]

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 4311764Sodium borohydride2×HCID 5284359Calcium ChlorideHCID 67111889HCID 67111889, compound

Product 1

HCID 67111738HCID 67111738, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of calcium chloride (0.159 g, 1.43 mmol) in 1.00 mL of water was added to a solution of diethyl 2-acetamido-2-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)malonate (0.330 g, 0.573 mmol) in THF (10.00 mL) and ethanol (10.00 mL). The reaction mixture was cooled to 0° C. in ice bath before the addition of sodium borohydride (0.108 g, 2.87 mmol); strong bubbled was observed and the solution became a yellow mixture. The reaction mixture was allowed to stir at ambient temperature for 2 h. DCM (5 mL) and additional sodium borohydride (0.108 g, 2.87 mmol) was added. After 18 h, the reaction mixture was poured over DCM/1 N HCl, and the organic layer was washed with 1 N HCl, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, 40 g column, 0-15% MeOH/DCM to give N-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1,3-dihydroxypropan-2-yl)acetamide. MS (ESI) m/z: calculated: 491.2; Observed: 492.1 (M++1).

Workup

  1. customstrong bubbled
  2. waitAfter 18 h
  3. washthe organic layer was washed with 1 N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography, 40 g column, 0-15% MeOH/DCM

Sources & evidence

ORD record
ord-f0edc6538ad84e569c6ed684b074aaae
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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