Potassium Carbonate → HCID 25000074, compound

HRID 424143Notes

Reaction equation

HRID 424143 reaction equation
C(C1C=C([CH2+]=NC2C=C[C:15]([O:16]C3C=CN=C(C(NC)=O)C=3)=[CH:14][C:13]=2F)N(C2C=CC=C(CO)C=2)N=1)(C)(C)C.[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48]([NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62]([NH:64][CH3:65])=[O:63])[CH:57]=3)=[CH:53][C:52]=2[F:68])=[O:49])[N:44]([C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([CH2:75][OH:76])[CH:70]=2)[N:43]=1)([CH3:41])([CH3:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+].C(Cl)(=O)CC>O1CCCC1>[C:15]([O:76][CH2:75][C:71]1[CH:72]=[CH:73][CH:74]=[C:69]([N:44]2[C:45]([NH:47][C:48](=[O:49])[NH:50][C:51]3[CH:67]=[CH:66][C:54]([O:55][C:56]4[CH:61]=[CH:60][N:59]=[C:58]([C:62](=[O:63])[NH:64][CH3:65])[CH:57]=4)=[CH:53][C:52]=3[F:68])=[CH:46][C:42]([C:38]([CH3:41])([CH3:39])[CH3:40])=[N:43]2)[CH:70]=1)(=[O:16])[CH2:14][CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 24829325HCID 24829325, compound

Product 1

HCID 25000074HCID 25000074, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of example 1, (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, (0.20 g, 0.38 mmol) and potassium carbonate (0.26 g, 1.88 mmol) in tetrahydrofuran (5 mL) was added dropwise propionyl chloride (0.05 mL, 0.56 mmol). The reaction mixture was allowed to stir at room temperature overnight. The crude material was concentrated and purified via prep-TLC (CH2Cl2:2M NH3 in MeOH, 97:3) to afford 0.09 g (42%) of the desired product as a white powder. MS m/z 589.1 (M+H)+; Retention time (LC-MS): 3.68 min.

Workup

  1. concentrationThe crude material was concentrated
  2. custompurified via prep-TLC (CH2Cl2:2M NH3 in MeOH, 97:3)

Sources & evidence

ORD record
ord-dd7e5d72bfcc47e2abea448e6ce8ee62
Source dataset
uspto-grants-2012_01
Patent number
US08101773B2

Reaction notes

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