Diisopropylethylamine → HCID 57827215, compound

HRID 1693253Notes

Reaction equation

HRID 1693253 reaction equation
C1CN([P+](ON2N=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:34][C:35]1[CH:36]=[CH:37][C:38]([F:61])=[C:39]([C@:41]23[CH2:49][C@@H:48]([O:50][CH2:51][CH3:52])[CH2:47][C@H:46]2[CH2:45][S:44][C:43]([NH:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[N:42]3)[CH:40]=1.C([N:65]([CH2:69]C)C(C)C)(C)C.C(=O)(O)[O-:72].[Na+]>ClCCl>[C:56]([O:55][C:54](=[O:60])[NH:53][C:43]1[S:44][CH2:45][C@@H:46]2[CH2:47][C@H:48]([O:50][CH2:51][CH3:52])[CH2:49][C@:41]2([C:39]2[CH:40]=[C:35]([NH:34][C:19]([C:24]3[CH:23]=[CH:22][C:21]([C:20]#[N:25])=[CH:69][N:65]=3)=[O:72])[CH:36]=[CH:37][C:38]=2[F:61])[N:42]=1)([CH3:57])([CH3:59])[CH3:58]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 57827362HCID 57827362, compound

Product 1

HCID 57827215HCID 57827215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBOP (205 mg) was added to a solution of tert-butyl(±)-[(4aR*,6S*,7aS*)-7a-(5-amino-2-fluorophenyl)-6-ethoxy-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]carbamate (52 mg), the compound of Preparation Example 26-(2) (27.3 mg) and N,N-diisopropylethylamine (0.26 mL) in dichloromethane (5.2 mL). The mixture was stirred at room temperature for one hour. The reaction solution was poured into a saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the title compound (45 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-05d015f1be4145fab35d7b6e815109f7
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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