Diisopropylethylamine → HCID 86728166, compound

HRID 627749Notes

Reaction equation

HRID 627749 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:35][CH2:34][CH2:33][C@@H:9]3[S:10](=[O:32])(=[O:31])[C:11]([CH3:30])([CH3:29])[C:12]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:13][C@:8]3([CH2:36][F:37])[C:6]=2[CH:7]=1.[C:38]([C:40]1[CH:41]=[C:42]([CH3:49])[C:43]([C:46](O)=[O:47])=[N:44][CH:45]=1)#[N:39].CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:38]([C:40]1[CH:41]=[C:42]([CH3:49])[C:43]([C:46]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[O:35][CH2:34][CH2:33][C@@H:9]4[S:10](=[O:32])(=[O:31])[C:11]([CH3:29])([CH3:30])[C:12]([N:14]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[N:13][C@:8]4([CH2:36][F:37])[C:6]=3[CH:7]=2)=[O:47])=[N:44][CH:45]=1)#[N:39]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 666658465-Cyano-3-methylpyridine-2-carboxylic acidHCID 86728113HCID 86728113, compound

Product 1

HCID 86728166HCID 86728166, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a 50-mL round-bottomed flask, tert-butyl N-[(4aS,11bS)-10-amino-11b-(fluoromethyl)-3,3-dimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (102 mg, 0.188 mmol), 5-cyano-3-methylpicolinic acid (36.6 mg, 0.226 mmol), Hunig's base (0.043 mL, 0.245 mmol), and 1-propanephosphonic acid cyclic anhydride (0.120 mL, 0.188 mmol) were added then dissolved in DCM (5 mL). The reaction mixture was stirred at RT for 3 h. The reaction mixture was then diluted with saturated NaHCO3 and extracted with EtOAc (15 mL). The organic extract was washed with water, brine (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give tert-butyl N-[(4aS,11bS)-10-[(5-cyano-3-methyl-pyridine-2-carbonyl)amino]-11b-(fluoromethyl)-3,3-dimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate as a white solid that was used without further purification. MS m/z=708.0 (M+Na).

Workup

  1. extractionextracted with EtOAc (15 mL)
  2. extractionThe organic extract
  3. washwas washed with water, brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9db5b382a26c4198801654094fd847af
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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