Acetic Acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879628
[C:1]([O:5][C@@H:6]([C:10]1[C:30]([CH3:31])=[CH:29][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:39][C:40]([CH3:42])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O>[C:1]([O:5][C@@H:6]([C:10]1[C:30]([CH3:31])=[CH:29][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][N:26]([CH:40]([CH3:42])[CH3:39])[CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 86700437(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid

Produkt 1

HCID 86700438(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid (30 mg, 0.055 mmol) in MeOH (1 mL) was added acetone (0.20 mL), acetic acid (0.08 mL), and sodium triacetoxyborohydride (58 mg, 0.27 mmol). Stirred at rt for 18 h then 60° C. for 3 h (reaction not to completion). H2O added (1 mL) and purified using reverse phase HPLC, eluting by 2-100% acetonitrile in H2O with 0.1% TFA to give the product. 1H NMR (400 MHz, CD3OD) δ 7.83 (s, 1H), 7.68 (m, 2H), 7.58 (m, 3H), 7.43 (t, J=8 Hz, 1H), 7.21 (d, J=8 Hz, 1H), 5.25 (s, 1H), 4.02 (m, 2H), 3.60 (m, 4H), 3.12 (m, 3H), 2.61 (s, 3H), 1.43 (d, J=7 Hz, 6H), 0.97 (s, 9H). LCMS-ESI+: calc'd for C33H39ClN3O3S: 592.2 (M+H+); Found: 592.3 (M+H+).

Aufarbeitung

  1. custom60° C. for 3 h (reaction not to completion)
  2. custompurified
  3. washeluting by 2-100% acetonitrile in H2O with 0.1% TFA
  4. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-0477f670ef80479faadd1b94414956ee
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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