Trifluoroacetic acid → HCID 73330929, compound

HRID 1055264Notes

Reaction equation

HRID 1055264 reaction equation
[C:1]([NH:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[C:18]2=[N:19][C:20]([CH3:42])=[C:21]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[C:36]5[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:35]=5[O:34][N:33]=4)[CH2:28][CH2:27]3)[C:22](=[O:23])[N:17]2[CH2:16][CH2:15][CH2:14]1)=[O:11])(=[O:6])[C:2](C)([CH3:4])C.F[C:44](F)(F)[C:45]([OH:47])=O.[CH:50]([N:53](C(C)C)CC)(C)[CH3:51].C(P(=O)(OCC)[O:62]CC)#N>ClCCl.O>[O:47]=[C:45]1[CH:44]=[CH:51][C:50](=[O:62])[N:53]1[CH2:4][CH2:2][C:1]([NH:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[C:18]2=[N:19][C:20]([CH3:42])=[C:21]([CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH:29]([C:32]4[C:36]5[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:35]=5[O:34][N:33]=4)[CH2:30][CH2:31]3)[C:22](=[O:23])[N:17]2[CH2:16][CH2:15][CH2:14]1)=[O:11])=[O:6]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 86711156HCID 86711156, compound

Product 1

HCID 73330929HCID 73330929, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl 3-pivalamidopropanoate, prepared as described in Step A, (901.5 mg, 1.15 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (5.7 mL) was stirred for 1 h at room temperature. To this mixture was carefully added a solution of N-maleoyl-3-aminopropionic acid (233.8 mg, 1.38 mmol), diisopropylethylamine (13.94 mL), diethyl cyanophosphonate (306.57 μL, 1.81 mmol) and dichloromethane (2 mL). The reaction mixture was stirred for 1 h at room temperature under argon atmosphere. The reaction mixture was poured into water (20 mL) and the aqueous layer extracted with dichloromethane (three times 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified on HPLC to give the title compound. ESI-MS (M+1) 649.

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (three times 20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude mixture was purified on HPLC

Sources & evidence

ORD record
ord-40e0f1c3480843d3b339f4ed1f071d19
Source dataset
uspto-grants-2016_07
Patent number
US09394354B2

Reaction notes

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