3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde → HCID 11998933, compound

HRID 1012938Notes

Reaction equation

HRID 1012938 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[CH2:34][S:33][C:32]2[CH:35]=[CH:36][C:37](C=O)=[N:38][C:31]=2[NH: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:37]4[CH:36]=[CH:35][C:32]5[S:33][CH2:34][C:29](=[O:28])[NH:30][C:31]=5[N:38]=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 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 126318584-Methoxy-1,3-benzothiazoleHCID 57699455HCID 57699455, compound

Product 1

HCID 11998933HCID 11998933, compound

Procedure

Using the same method as for Example 23, steps 23.a to 23.f, the title compound was synthesised from 4-methoxybenzothiazole, (3R,6S)-(6-formyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde. After chromatography on SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether/MeOH, a yellowish solid (30 mg) was obtained.

Workup

  1. customAfter chromatography on SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) and crystallisation from ether/MeOH

Sources & evidence

ORD record
ord-1dc32f683a7a420a95b8dd49633b3d6c
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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