Trifluoroacetic acid → HCID 10211523, compound

HRID 489685Notes

Reaction equation

HRID 489685 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([S:48]([CH3:51])(=[O:50])=[O:49])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:47])[C@H:18]([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][N:31]2C(OC(C)(C)C)=O)=[O:29])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:13][CH2:12]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][N:4]([S:48]([CH3:51])(=[O:49])=[O:50])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:47])[C@H:18]([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][NH:31]2)=[O:29])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69152743HCID 69152743, compound

Product 1

HCID 10211523HCID 10211523, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) from tert-butyl 3-{N-[(1R)-2-(4-(2-[(2-aminoethyl)-(methylsulfonyl)amino]phenyl}piperidyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl]carbamoyl}(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step f) (294.8 mg, 0.4 mmol) and 50% TFA in CH2Cl2 (20 mL). Purification by reverse phase preparative HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min] provided the title compound (TFA salt) as a white solid (224 mg). MS (ESI, pos. ion) m/z: 638 (M+1); (ESI, neg. ion) m/z: 636 (M−1). Calc'd for C33H40ClN5O4S: 637.25. Anal. Calcd for C33H40ClN5O4S.2.5C2H3O2: C, 49.43; H, 4.64; N, 7.41. Found: C, 49.39; H, 4.78; N, 7.58.

Workup

  1. customThe title compound was prepared
  2. customPurification by reverse phase preparative HPLC [Phenomenex

Sources & evidence

ORD record
ord-4ced97386e80496ebd9ad56a7f957073
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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