Metaperiodic acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxotetrahydropyrimidin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879328Notes

Reaction equation

HRID 879328 reaction equation
[I:1]([OH:5])(=[O:4])(=[O:3])=[O:2].[O-2:6].[O-2].[O-2].[Cr+6:9].[C:10]([O:14][C@@H:15]([C:18]1[C:43]([CH3:44])=[CH:42][C:21]2[N:22]=[C:23]([N:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[N:36]([CH3:40])[N:35]=[CH:34]5)[C:26]3=[O:41])[S:24][C:20]=2[C:19]=1[C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)[CH2:16][OH:17])([CH3:13])([CH3:12])[CH3:11]>C(#N)C>[I:1]([OH:5])(=[O:4])(=[O:3])=[O:2].[O-2:14].[O-2:6].[O-2:2].[Cr+6:9].[C:10]([O:14][C@@H:15]([C:18]1[C:43]([CH3:44])=[CH:42][C:21]2[N:22]=[C:23]([N:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[N:36]([CH3:40])[N:35]=[CH:34]5)[C:26]3=[O:41])[S:24][C:20]=2[C:19]=1[C:45]1[CH:46]=[CH:47][C:48]([Cl:51])=[CH:49][CH:50]=1)[C:16]([OH:6])=[O:17])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 65185Metaperiodic acidHCID 10219390chromium (VI) trioxideHCID 86699844(S)-1-(6-(1-tert-butoxy-2-hydroxyethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-3-(1-methyl-1H-indazol-5-yl)tetrahydropyrimidin-2(1H)-one

Product 2

HCID 86699846(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxotetrahydropyrimidin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acidHCID 131721976Periodic acid chromium trioxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

. A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol %) in wet acetonitrile (0.75% H2O, 114 mL). To a solution of (S)-1-(6-(1-tert-butoxy-2-hydroxyethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-3-(1-methyl-1H-indazol-5-yl)tetrahydropyrimidin-2(1H)-one (16 mg) in wet acetonitrile (1.0 mL, 0.75% H2O) at 0° C. was added the above stock solution (0.6 mL) at 0° C. Filtration and purification by reverse phase HPLC gave (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxotetrahydropyrimidin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C32H32ClN5O4S: 618.2 (M+H+); Found: 618.3 (M+H+), 615.8 (M+H+); 1H-NMR 400 MHz, (CD3OD) δ 7.99 (s, 1H), 7.70 (s, 1H), 7.62-7.50 (m, 3H), 7.50-7.47 (m, 3H), 7.37 (m, 1H), 5.20 (s, 1H), 4.40 (m, 2H), 4.07 (s, 3H), 3.85 (m, 2H), 2.55 (s, 3H), 2.34 (m, 2H), 0.94 (s, 9H).

Workup

  1. filtrationFiltration and purification by reverse phase HPLC

Sources & evidence

ORD record
ord-f4db0cd70ee548bb991e5adde4e58c8b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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