Water → HCID 66712512, compound

HRID 1262138Notes

Reaction equation

HRID 1262138 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[CH:16][C:15]3=[CH:18][CH:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([S:27](=[O:34])(=[O:33])[NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=4)[N:14]3[N:13]=2)[CH:6]=1)C.O>[OH-].[Na+].C1COCC1>[C:29]([NH:28][S:27]([C:23]1[CH:22]=[C:21]([C:20]2[N:14]3[C:15]([CH:16]=[N:17][C:12]([NH:11][C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:4]([OH:35])=[O:3])=[N:13]3)=[CH:18][CH:19]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:33])=[O:34])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 962WaterHCID 66712132HCID 66712132, compound

Product 1

HCID 66712512HCID 66712512, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-benzoic acid ethyl ester (77.0 mg, 0.156 mmol) was taken up in 2 M of Sodium hydroxide in water (2.00 mL, 5.00 mmol) and 2 ml THF, heated for 72 h at 60° C. Concentrated down THF, neutralized aq layer, and extracted with CH2Cl2. Dried, filtered, and concentrated. Took residue up in DMSO and purified by Gilson RP-HPLC. LCMS=465.9 (M+H), HPLC rt=3.199, purity=98%. 1H NMR (400 MHz, CDCl3, δ, ppm): 12.95 (bs, 1H), 9.74 (s, 1H), 9.07 (s, 1H), 8.42 (d, J=7.6 Hz, 1H), 8.44 (s, 1H), 8.26 (s, 1H), 8.07 (d, J=8.3 Hz, 1H), 7.72 (dd, J=8.3 Hz, 7.6 Hz, 1H), 7.61 (s, 1H), 7.55 (d, J=8.3 Hz, 1H), 7.47 (dd, J=7.6 Hz, 8.3 Hz, 1H), 7.24 (d, J=4.6 Hz, 1H), 7.04 (d, J=4.9 Hz, 1H), 1.1 (s, 9H).

Workup

  1. concentrationConcentrated down THF, neutralized aq layer
  2. extractionextracted with CH2Cl2
  3. customDried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customTook residue up in DMSO and purified by Gilson RP-HPLC
  7. customLCMS=465.9 (M+H), HPLC rt=3.199, purity=98%

Sources & evidence

ORD record
ord-eedec1e5837e4ccfb55be5bd57eaa560
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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