Diisopropylethylamine → HCID 44817105, compound

HRID 1671296Notes

Reaction equation

HRID 1671296 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH2:18][CH3:19])[C:15]([C:20](O)=[O:21])=[C:11]2[O:12][C:13]=1[CH3:14].[CH:23]1([CH2:26][NH:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH:23]1([CH2:26][N:27]([CH2:28][CH2:29][CH3:30])[C:20]([C:15]2[C:16]([CH2:18][CH3:19])=[N:17][N:10]3[C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])=[C:13]([CH3:14])[O:12][C:11]=23)=[O:21])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59186045HCID 59186045, compound

Product 1

HCID 44817105HCID 44817105, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-(2,4-dichloro-phenyl)-6-ethyl-2methyl-pyrazolo[5,1-b]oxazole-7-carboxylic acid (Intermediate IA) (37 mg, 0.11 mmol, 1 eq.) in DMF (0.8 ml) is successively added cyclopropylmethyl-propylamine (0.017 ml, 0.12 mmol, 1.1 eq.), DIPEA (0.038 ml, 0.22 mmol, 2 eq.) and HATU (46 mg, 0.12 mmol, 1.1 eq.) at RT. The reaction mixture is heated at 50° C. for 2 h then poured into EtOAc and washed with K2CO3 2M in water (2×). The organic layer is dried over Na2SO4, filtered and concentrated to dryness and the resulting crude residue is purified by column chromatography (SiO2; gradient elution iso-hexane/EtOAc 6:1 to 1:1) to yield the title compound as a yellow oil. MS: m/z 434.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.90 (1H, d), 7.73 (1H, d), 7.65 (1H, dd), 3.46 (2H, t), 3.30 (2H, s), 2.70 (2H, q), 2.34 (3H, s), 1.60 (2H, m), 1.11 (3H, t), 1.02 (1H, m), 0.63 (3H, m), 0.48 (2H, m), 0.20 (2H, m).

Workup

  1. customat RT
  2. washwashed with K2CO3 2M in water (2×)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customthe resulting crude residue is purified by column chromatography (SiO2; gradient elution iso-hexane/EtOAc 6:1 to 1:1)

Sources & evidence

ORD record
ord-cfe1a63c58d04084bd1c2fa3ec149e08
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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