Diisopropylethylamine → HCID 57827714, compound

HRID 1693250Notes

Reaction equation

HRID 1693250 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:60])=[C:39]([C@:41]23[CH2:49][C@@H:48]([O:50][CH3:51])[CH2:47][C@H:46]2[CH2:45][S:44][C:43]([NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[N:42]3)[CH:40]=1.C([N:64]([CH2:68]C)C(C)C)(C)C.C(=O)(O)[O-:71].[Na+]>ClCCl>[C:55]([O:54][C:53](=[O:59])[NH:52][C:43]1[S:44][CH2:45][C@@H:46]2[CH2:47][C@H:48]([O:50][CH3:51])[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:68][N:64]=3)=[O:71])[CH:36]=[CH:37][C:38]=2[F:60])[N:42]=1)([CH3:56])([CH3:57])[CH3:58]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 57827202HCID 57827202, compound

Product 1

HCID 57827714HCID 57827714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBOP (86.9 mg) was added to a solution of tert-butyl(−)-[(4aR*,6S*,7aS*)-7a-(5-amino-2-fluorophenyl)-6-methoxy-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]carbamate (22 mg), the compound of Preparation Example 26-(2) (11.6 mg) and N,N-diisopropylethylamine (0.11 mL) in dichloromethane (2.2 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 (29 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-b495657f17b74f7793c80f019e3a3fcb
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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