Water → HCID 66780212, compound

HRID 1470352Notes

Reaction equation

HRID 1470352 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[N:24][N:25]([CH2:27][C:28]([OH:30])=O)[CH:26]=3)[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].S(Cl)(Cl)=O.[OH-].[NH4+:36].O>C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[N:24][N:25]([CH2:27][C:28]([NH2:36])=[O:30])[CH:26]=3)[CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl Chloride3×HCID 66779037HCID 66779037, compound

Product 1

HCID 66780212HCID 66780212, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]pyrazol-1-yl]acetic acid (0.040 mmol) is dissolved in THF and thionylchloride (0.234 mmol) is added. The mixture is stirred 24 h at RT. Additional thionylchloride (0.234 mmol) is added and the reaction is stirred 24 h at RT. Additional Thionylchlorid (2.343 mmol) is added and the reaction is stirred 48 h. The solvent is removed in vacuo and ammonium hydroxide (32%, 1.205 mmol) is added. Water (3 ml) is added and the precipitate is filtered and resuspended in MeOH and filtered and dried at 50° C. in vacuo. The product is isolated as beige solid in a yield of 92%). HPLC (method A): Rt 2.40 min (purity 95%); LCMS (ESI+) (method E): Rt 1.49 min, M+H+ 409.1 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.67 (s, 1H), 8.45 (d, J=4.4, 1H), 8.32 (s, 1H), 7.75-7.51 (m, 3H), 7.47-7.26 (m, 3H), 4.93 (s, 2H), 3.95 (s, 6H), 3.74 (s, 3H).

Workup

  1. stirringthe reaction is stirred 24 h at RT
  2. stirringthe reaction is stirred 48 h
  3. additionis added
  4. filtrationthe precipitate is filtered
  5. filtrationfiltered
  6. customdried at 50° C. in vacuo
  7. customThe product is isolated as beige solid in a yield of 92%)

Sources & evidence

ORD record
ord-2b26a2ea1f354541bc8a85c3ed6d1495
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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