Diisopropylethylamine → HCID 10323110, compound

HRID 2375435Notes

Reaction equation

HRID 2375435 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[F:10][C:11]1[CH:22]=[CH:21][C:14]2[C:15](=S)[NH:16][C:17](=[O:19])[O:18][C:13]=2[CH:12]=1.[C:23]([C:25]1([NH:34][C:35](=[O:45])[CH:36]([NH2:44])[CH2:37][CH2:38][C:39]([CH3:43])([CH3:42])[CH2:40][CH3:41])[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]1)#[N:24].C(N(CC)C(C)C)(C)C>C1COCC1>[C:23]([C:25]1([NH:34][C:35](=[O:45])[CH:36]([NH:44][C:15]2[C:14]3[CH:21]=[CH:22][C:11]([F:10])=[CH:12][C:13]=3[O:18][C:17](=[O:19])[N:16]=2)[CH2:37][CH2:38][C:39]([CH3:43])([CH3:42])[CH2:40][CH3:41])[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][CH3:33])[CH2:29][CH2:30]1)#[N:24]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 225663437-Fluoro-4-thioxo-3,4-dihydro-benzo[e][1,3]oxazin-2-oneHCID 59654225HCID 59654225, compound

Product 1

HCID 10323110HCID 10323110, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (365 mg, 1.43 mmol, 1.00 eq) was added to a suspension of 7-fluoro-4-thioxo-3,4-dihydro-benzo[e][1,3]oxazin-2-one (280 mg, 1.42 mmol, 1.00 eq), 2-amino-5,5-dimethyl-heptanoic acid (4-cyano-1-propyl-piperidin-4-yl)-amide (627 mg, 1.42 mmol, 1.00 eq), and N,N-diisopropyl ethylamine (1.00 mL, 5.74 mmol, 4.04 eq) in THF (10.0 mL). The reaction mixture was stirred at room temperature overnight, then concentrated, resuspended in ethyl acetate (50 mL) and washed with saturated Na2CO3 solution. The organic phase was dried (MgSO4) and concentrated and the resulting residue was chromatographed over silica gel using a gradient of methanol in dichloromethane as the eluant to provide 324 mg (47% yield) of the title compound; m/z calculated for C26H36F N5O3 485.6, found 486.5 (M+H)+.

Workup

  1. concentrationconcentrated
  2. washwashed with saturated Na2CO3 solution
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customthe resulting residue was chromatographed over silica gel using a gradient of methanol in dichloromethane as the eluant

Sources & evidence

ORD record
ord-9ae8f480874143ed8cb77e01dd3c42af
Source dataset
uspto-grants-2008_12
Patent number
US07465745B2

Reaction notes

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