Triethylamine → HCID 24871527, compound

HRID 1673247Notes

Reaction equation

HRID 1673247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C@H:25]([NH2:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[CH3:29][C:30]1[NH:34][N:33]=[C:32]([C:35](O)=[O:36])[CH:31]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C@H:25]([NH:26][C:35]([C:32]4[CH:31]=[C:30]([CH3:29])[NH:34][N:33]=4)=[O:36])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 2724699PyBOPHCID 67019951HCID 67019951, compound

Product 1

HCID 24871527HCID 24871527, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Step B (300 mg, 0.69 mmol), 5-methylpyrazole-3-carboxylic acid (105 mg, 0.83 mmol), PyBOP (540 mg, 1.04 mmol), and NEt3 (0.19 mL, 1.38 mmol) in 20 mL of CH2Cl2 was stirred at rt. After 16 h, the reaction mixture was diluted with Et2O (50 mL), washed with saturated aq NaHCO3 (3×50 mL) and brine (3×50 mL). The organic layer was separated, dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 1:1 v/v EtOAc/Hexanes as the eluant afforded the title compound: 1H NMR δ 1.44 (s, 3H), 1.51 (s, 3H), 1.94 (t, J=12.5, 1H), 2.26-2.30 (m, 4H), 5.62 (m, 1H), 6.58 (s, 1H), 6.96 (d, J=8.5, 2H), 7.12-7.29 (m, 5H), 7.69 (s, 1H).

Workup

  1. washwashed with saturated aq NaHCO3 (3×50 mL) and brine (3×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0b29dbcdd484017ad41cc657e3333eb
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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