Water → N-[(2-Aminoethoxy)acetyl]-5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide hydrochloride

HRID 421576Notes

Reaction equation

HRID 421576 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C:24]4=[O:29])=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.[OH2:30].Cl(O)(=O)(=O)=O>C(#N)C>[ClH:1].[NH2:9][CH2:10][CH2:11][O:30][CH2:5][C:7]([N:9]([CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[CH:21][CH:22]=2)[CH2:12]1)[C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:8])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 9875401Rivaroxaban

Product 1

HCID 66674124N-[(2-Aminoethoxy)acetyl]-5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Agilent 1100 with DAD (G1315A), quat. pump (G1311A), autosampler CTC HTS PAL, degasser (G1322A) and column thermostat (G1316A); column: Zorbax Extend-C18 3.5μ; temperature: 40° C.; eluent A: water+5 ml of perchloric acid/liter, eluent B: acetonitrile; flow rate: 0.7 ml/min; gradient: 0-0.5 min 98% A, 2% B; ramp 0.5-4.5 min 10% A, 90% B; 4.5-6 min 10% A, 90% B; ramp 6.5-6.7 min 98% A, 2% B; 6.7-7.5 min 98% A, 2% B.

Workup

  1. custom40° C.
  2. custom0-0.5 min 98% A, 2% B
  3. customramp 0.5-4.5 min 10% A, 90% B
  4. custom4.5-6 min 10% A, 90% B
  5. customramp 6.5-6.7 min 98% A, 2% B
  6. custom6.7-7.5 min 98% A, 2% B

Sources & evidence

ORD record
ord-9d144c270eee4eea939c8c0bb4b50ce8
Source dataset
uspto-grants-2012_01
Patent number
US08101601B2

Reaction notes

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