HCID 131730309, compound → HCID 131730308, compound

HRID 1948287Notes

Reaction equation

HRID 1948287 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]([C:19]3[NH:20][C:21]([CH3:25])=[C:22]([Cl:24])[CH:23]=3)=[O:18])[C@H:12]([O:26][CH3:27])[CH2:11]2)=[N:7][C:6]=1[C:28]([NH:30]C(C)(C1C=CC=CC=1)C)=[O:29])=[O:4]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:30][C:28]([C:6]1[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]([C:19]3[NH:20][C:21]([CH3:25])=[C:22]([Cl:24])[CH:23]=3)=[O:18])[C@H:12]([O:26][CH3:27])[CH2:11]2)[S:9][C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[O:29]

Participants

4

Reactant 1

HCID 131730309HCID 131730309, compound

Product 1

HCID 131730308HCID 131730308, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
85 °C

Procedure

Cis(±)methyl-2-(4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-{[(1-methyl-1-phenylethyl)amino]carbonyl}-1,3-thiazole-5-carboxylate (Example 21; 0.058 g, 0.1 mmol) was dissolved in equal volumes of TFA and DCM. The reaction was heated in a sealed tube to an external temperature of 85° C. overnight. The reaction mixture was concentrated to remove the DCM and excess TFA. The residue was partitioned with EtOAc and NaHCO3 and the organic extracts were dried with MgSO4 and concentrated to a yellow solid (0.050 g, 100%). MS (ES) MH+: 456 for C18H22ClN5O5S.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the DCM and excess TFA
  3. customThe residue was partitioned with EtOAc and NaHCO3
  4. dry with materialthe organic extracts were dried with MgSO4
  5. concentrationconcentrated to a yellow solid (0.050 g, 100%)

Sources & evidence

ORD record
ord-100e70a9ec8147b2b87183cf9b751869
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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