Hydrochloric Acid → Racemic-4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoic acid

HRID 410686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410686
[OH:1][C:2]([C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=1)([C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=3)[CH:13]=[C:12]([CH3:27])[CH:11]=2)=[CH:8][N:9]=1)[CH2:3][OH:4].CO.[OH-].[Na+].Cl>O>[OH:1][C:2]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:36][CH:37]=1)([C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:24])([F:26])[F:25])[CH:20]=[CH:19][N:18]=3)[CH:13]=[C:12]([CH3:27])[CH:11]=2)=[CH:8][N:9]=1)[CH2:3][OH:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67433739Methyl 4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoate

Produkt 1

HCID 67248048Racemic-4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoic acidAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A microwave vial was charged with the product of Step 2 (50 mg, 0.094 mmol), MeOH (666 μl) and then NaOH (700 μl, 0.700 mmol). The mixture was irradiated in the microwave for 20 minutes at 100° C. The pH was adjusted to 3-4 with 1M HCl, then diluted with water and extracted with 10% IPA/CHCl3. The combined organics were washed with water, dried (NaSO4), filtered and concentrated to afford racemic-4-{1,2-dihydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoic acid (33.4 mg, 0.065 mmol, 68.6% yield). MS ESI: [M+H]+ m/z 517.1. 1H NMR (500 MHz, DMSO-d6) δ 12.86 (s, 1H), 10.24 (s, 1H), 8.82 (d, J=4.8, 1H), 7.99 (s, 1H), 7.93-7.85 (m, 3H), 7.74 (d, J=8.3, 2H), 7.45 (s, 1H), 7.26 (d, J=4.8, 1H), 7.12 (s, 1H), 6.73 (s, 1H), 5.11 (t, J=5.8, 1H), 4.10 (dd, J=5.6, 11.2, 1H), 4.04-3.89 (m, 1H), 2.31 (s, 3H).

Aufarbeitung

  1. customThe mixture was irradiated in the microwave for 20 minutes at 100° C
  2. extractionextracted with 10% IPA/CHCl3
  3. washThe combined organics were washed with water
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9359282ff44b406388c5dbbbc67c763d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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