Phenyl methyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate → Phenyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate

HRID 424487Notes

Reaction equation

HRID 424487 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:15]1=2)[C:3](=[O:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCCC1.C(O)C.[Pd]>[NH2:24][C:21]1[CH:22]=[CH:23][C:15]2[N:14]([CH2:13][CH2:12][N:2]([CH3:1])[C:3](=[O:11])[O:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:19][CH2:18][S:17][C:16]=2[CH:20]=1

Participants

5

Reactant 1

HCID 59144104Phenyl methyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate

Product 1

HCID 59144153Phenyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamateYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenyl methyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (100 mg, 0.268 mmol) in tetrahydrofuran (4 mL) and ethanol (4.00 mL) under argon was added 10% Pd—C (28.5 mg, 0.027 mmol). The resulting mixture was stirred at room temperature overnight under an atmosphere of hydrogen (balloon pressure). The mixture was then filtered through a pad of Celite and concentrated, giving the desired product (81 mg, 88%) as a dark oil. MS-EI: (m/z, %) 343 (M+, 64), 179 (100), 151 (45).

Workup

  1. filtrationThe mixture was then filtered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3359955e8f3d437c9f1f756bdea44d85
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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