Sodium hydride → HCID 86759168, compound

HRID 1167384Notes

Reaction equation

HRID 1167384 reaction equation
[OH:1][C:2]1[N:3]=[CH:4][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10]=2[N:11]=1.[H-].[Na+].Br[CH2:19][C:20]([N:22]([CH2:29][CH:30]([NH2:38])[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21]>CN(C=O)C>[OH:1][CH:2]1[N:11]([CH2:19][C:20]([N:22]([CH2:29][CH:30]([NH2:38])[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])[C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86759169HCID 86759169, compoundHCID 178517551HCID 178517551, compound

Product 1

HCID 86759168HCID 86759168, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-10-H-pyrimido[5,4-b][1,4]benzothiazin (653 mg, 3.0 mmol) was suspended in DMF (30 mL) and NaH (60% in mineral oil, 132 mg, 3.3 mmol) was added in one portion. After 15 minutes ethyl N-bromoacetyl-N-(2-Boc-aminoethyl)-glycinate (1.10 g, 3.3 mmol) was added. The mixture was stirred at room temperature for 2 hours, evaporated in vacuo, redissolved in dichloromethane (200 mL) and washed once with saturated aqueous NaHCO3 (100 mL) and once with saturated aqueous NaCl. The mixture was dried (MgSO4) and evaporated to dryness in vacuo. The crude material was purified on a silica gel column using methanol/dichloromethane (1:9, v/v) as the eluent to give 853 mg (57%) of the title compound.

Workup

  1. customevaporated in vacuo
  2. dissolutionredissolved in dichloromethane (200 mL)
  3. washwashed once with saturated aqueous NaHCO3 (100 mL) and once with saturated aqueous NaCl
  4. dry with materialThe mixture was dried (MgSO4)
  5. customevaporated to dryness in vacuo
  6. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-55eddaadd3a042b7af49ef7716bd2469
Source dataset
uspto-grants-2003_09
Patent number
US06617422B1

Reaction notes

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