Triethylamine → HCID 86714643, compound

HRID 1409379Notes

Reaction equation

HRID 1409379 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:27](O)([CH3:29])[CH3:28])[O:25][CH:26]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9].C(N(CC)CC)C.P([Cl:46])(OCC)(OCC)=O.[OH-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][CH:17]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C@@H:27]([CH2:29][Cl:46])[CH3:28])[O:25][CH:26]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([F:10])[C:7]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 14798Sodium HydroxideHCID 70655864HCID 70655864, compound

Product 1

HCID 86714643HCID 86714643, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)—N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(2-hydroxypropan-2-yl)oxazole-4-carboxamide (0.116 mmol, 0.05 g) was dissolved in DMF (5 ml) and triethylamine (0.255 mmol, 0.026 g) was added. Diethyl chlorophosphate (0.232 mmol, 0.040 g) was carefully added with a syringe. The resulting mixture was stirred at RT overnight. A mixture of ice and water was added and the mixture was neutralized with 1 M NaOH. The mixture was extracted twice with DCM. The combined organics were washed with water, dried, filtered and evaporated. The crude product was purified by preparative HPLC. 0.0047 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.26 (d, 3H), 2.04 (d, 6H), 4.29-4.36 (m, 1H), 4.38-4.46 (m, 1H), 4.54-4.66 (m, 1H), 6.64 (d, 1H), 7.39 (d, 1H), 7.51 (d, 1H), 7.61 (dd, 1H), 7.72-7.75 (m, 1H), 8.17 (s, 1H).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted twice with DCM
  3. washThe combined organics were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cd30bbaca4e74e639f71f3c9db6201b5
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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