Dimethylformamide → HCID 10311699, compound

HRID 497436Notes

Reaction equation

HRID 497436 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[N:10]2)=[CH:5][CH:4]=1.[CH3:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.CN([P+](ON1N=[N:46][C:45]2[C:40]1=CC=C[CH:44]=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[CH3:55][N:56]([CH:58]=O)[CH3:57]>>[OH:25][CH2:26][CH2:27][N:22]([CH2:23][C:24]1[CH:5]=[CH:4][CH:3]=[CH:8][C:55]=1[N:56]1[CH2:58][CH2:44][CH:45]([NH:46][C:14]([C:13]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[N:10]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:16])[CH2:40][CH2:57]1)[CH3:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 111619581-(4-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 10311699HCID 10311699, compoundYield 23%

Procedure

A small reaction vessel was charged with the compound of from Part A (0.053 g, 0.20 mmol), 2-(4-Methoxyphenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (0.037 g, 0.13 mmol), 4-methylmorpholine (36 ul, 0.33 mmol) and DMF (3 mL). While stirring under N2, Castro's Reagent (0.089 g, 0.20 mmol) was added and the reaction mixture was allowed to stir at room temperature for 48 h. The reaction was concentrated and purified by prep LC/MS to obtain the target compound. (0.016 g, 23% yield). 1HNMR (DMSO-d6) δ 8.72 (d, 1H), 7.50-7.41 (m, 7H), 7.34-7.23 (t, 1H), 7.08-7.03 (d, 2H), 4.49-4.45 (m, 2H), 3.81 (s, 3H), 3.77 (m, 2H), 3.14 (m, 2H), 2.98 (m, 2H), 2.80 (bs, 4H), 1.89 (m, 2H), 1.71 (m, 2H); MS (ESI+) m/z 532.5, (M+H)+.

Workup

  1. stirringto stir at room temperature for 48 h
  2. concentrationThe reaction was concentrated
  3. custompurified by prep LC/MS
  4. customto obtain the target compound

Sources & evidence

ORD record
ord-03d550bddb44485da7e34653399e8e35
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

Loading…