Triethylamine → HCID 59026185, compound

HRID 639116Notes

Reaction equation

HRID 639116 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[O:40]=[C:41]1[CH2:46][S:45][C:44]2[CH:47]=[CH:48][C:49]([C:51](O)=[O:52])=[N:50][C:43]=2[NH:42]1>CN(C=O)C>[CH3:1][N:2]([CH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1)[C:51]([C:49]1[CH:48]=[CH:47][C:44]2[S:45][CH2:46][C:41](=[O:40])[NH:42][C:43]=2[N:50]=1)=[O:52]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidHCID 53249193tert-Butyl 3-[(methylamino)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 59026185HCID 59026185, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-[(methylamino)methyl]-1-pyrrolidinecarboxylate (153 mg, 0714 mmol) in DMF (2 mL) were added triethylamine (0.1 mL, 0.714 mmol) followed by DPPA (0.154 mL, 0.714 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (150 mg, 0.714 mmol). After stirring at room temperature for 24 h, the solution was partitioned between ethyl acetate and K CO solution (5% in H O). The aqueous layer was extracted several times with ethyl acetate. The organic fractions were combined, dried over MgSO, concentrated and purified with column chromatography (silica, 0-5% MeOH in DCM) to provide the title compound as an off-white solid (240 mg, 83%): LC/MS (ES) m/e 407 (M+H).

Workup

  1. customthe solution was partitioned between ethyl acetate and K CO solution (5% in H O)
  2. extractionThe aqueous layer was extracted several times with ethyl acetate
  3. dry with materialdried over MgSO
  4. concentrationconcentrated
  5. custompurified with column chromatography (silica, 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-ed3f78340c6347b5a587fb7b7a00a0fe
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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