3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehyde → HCID 11998934, compound

HRID 1012939Notes

Reaction equation

HRID 1012939 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(O[C:17](=O)[NH:18][C@@H:19]1[CH2:24][CH2:23][C@@H:22]([CH:25]=[O:26])[O:21][CH2:20]1)(C)(C)C.[O:28]=[C:29]1[NH:34][C:33]2[CH:35]=[C:36](C=O)[CH:37]=[CH:38][C:32]=2[S:31][CH2:30]1>>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:25]([C@H:22]3[O:21][CH2:20][C@H:19]([NH:18][CH2:17][C:36]4[CH:37]=[CH:38][C:32]5[S:31][CH2:30][C:29](=[O:28])[NH:34][C:33]=5[CH:35]=4)[CH2:24][CH2:23]3)=[O:26])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 126318584-Methoxy-1,3-benzothiazoleHCID 57699455HCID 57699455, compound

Product 1

HCID 11998934HCID 11998934, compound

Procedure

Using the same protocol as for example 23, steps 23.a) to 23.f, the title compound was synthesised using 4-methoxybenzothiazole (8.7 mmol), (3R,6S)-(6-formyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (4.6 mmol) and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbaldehyde (0.7 mmol) and obtained after chromatography on SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether/MeOH as a yellowish solid (35 mg).

Workup

  1. customobtained after chromatography
  2. customon SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether/MeOH as a yellowish solid (35 mg)

Sources & evidence

ORD record
ord-d7398600e86f4b68a23329a91ec15738
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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