Trifluoroacetic acid → HCID 10210143, compound

HRID 489667Notes

Reaction equation

HRID 489667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34]([CH:36]2[CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37]2)=[O:35])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34]([CH:36]2[CH2:39][NH:38][CH2:37]2)=[O:35])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23587442Tert-butyl 3-(n-[(1r)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]carbamoyl)azetidine-carboxylate

Product 1

HCID 10210143HCID 10210143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) using tert-butyl 3-(N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}piperidyl)-2-oxoethyl]carbamoyl)azetidine-carboxylate (Step a) (565 mg, 0.84 mmol) and 50% TFA in CH2Cl2 (6 mL). Purification by reverse phase preparative HPLC [YMC-Pack ODS-AM 250×20 mm 5 μm column, 40% to 75% CH3CN (0.1% TFA) in H2O(0.1% TFA) over 10 min] provided the title compound (TFA salt) as an amorphous white solid (420 mg). MS (ESI, pos. ion) m/z: 573 (M+1). Calcd for C29H37ClN4O4S: 572.22. Anal. Calcd for C29H37ClN4O4S 1.7C2HF3O2: C, 50.74; H, 5.09; N, 7.30, S, 4.18. Found: C. 50.47; H, 5.03; N, 7.36; S, 4.28.

Workup

  1. customThe title compound was prepared
  2. customPurification by reverse phase preparative HPLC [YMC-Pack ODS-AM 250×20 mm 5 μm column, 40% to 75% CH3CN (0.1% TFA) in H2O(0.1% TFA) over 10 min]

Sources & evidence

ORD record
ord-8d99ee1763064ad49cd457810cb25a95
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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