Hydrochloric Acid → HCID 10144296, compound

HRID 228121Notes

Reaction equation

HRID 228121 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N: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)[CH3:3].Cl>O1CCOCC1>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N: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)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69076794Tert-butyl 3-{n-[(1r)-2-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl]carbamoyl}(3s)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate

Product 1

HCID 10144296HCID 10144296, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To tert-butyl 3-{N-[(1R)-2-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl]carbamoyl}(3S)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate (Step 5) (0.31 g, 0.47 mmol) dissolved in dioxane (0.5 mL) was added 4N HCl in dioxane (1 mL). After stirring at RT for 6 h, the solvent was removed in vacuo, and the residue was purified by preparative HPLC (Waters Xterra C18 5 micron 100×20 mm, 10% to 80% CH3CN in H2O over 6.0 min, 4.63 min) to give N-[(1R)-2-(4-{2-[(dimethylamino)methyl]phenyl}piperazinyl)-1-[(4-chlorophenyl)methyl]-2-oxoethyl]((3S)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide (TFA salt) as a white solid (0.27 g). MS m/z: 560 (M+H). Calc'd for C32H38ClN5O2: 559.27. Anal. Calcd for C32H38ClN5O2-2.5 TFA-0.1 H2O: C, 52.47; H, 4.84; N, 8.27; Cl, 4.19. Found: C, 52.26; H, 4.75; N, 8.14; Cl, 4.41.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (Waters Xterra C18 5 micron 100×20 mm, 10% to 80% CH3CN in H2O over 6.0 min, 4.63 min)

Sources & evidence

ORD record
ord-40048401a17a4cccb37309e66e9c885e
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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