Hydrochloric Acid → HCID 21060089, compound

HRID 228125Notes

Reaction equation

HRID 228125 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:24][C:25]([O:27]C(C)(C)C)=O)[C:10](=[O:23])[N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl.CCN(C(C)C)C(C)C.[N:42]1([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][C@H:43]1[C:52]([OH:54])=O.CCN=C=NCCCN(C)C.CI.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:24][C:52]([C@@H:43]2[CH2:44][C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:51][N:42]2[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])=[O:54])[C:10](=[O:23])[N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:16]2)=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:24][C:25]([C@@H:43]2[CH2:44][C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:51][NH:42]2)=[O:27])[C:10](=[O:23])[N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 10236463N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide methyliodideHCID 21060090HCID 21060090, compound

Product 2

HCID 21060089HCID 21060089, compoundYield 152.1%HCID 69078990HCID 69078990, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(N-{(1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-(2-pyridyl)piperazinyl)ethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared from N-{(1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-(2-pyridyl)piperazinyl)ethyl}(tert-butoxy)-carboxamide (Step 1) (800 mg, 1.80 mmol), following the procedure for Example 93, Step 2 using 25 mL of EtOAc satd with HCl for the first step, and DIEA (240 μl, 1.38 mmol), Boc-L-Tic-OH (340 mg, 1.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide (740 mg, 2.5 mmol), HOAT (184 mg, 1.35 mmol) and DMF (15 mL) for the second step. The crude was purified by flash chromatography (SiO2, 1:1, hexane:EtOAc) to yield the title compound (460 mg). MS (ESI, pos. ion) m/z: 604 (M+H), (ESI, neg. ion) m/z: 602 (M−H). Calc'd for C33H38ClN5O4: 604.14.

Workup

  1. customThe crude was purified by flash chromatography (SiO2, 1:1, hexane:EtOAc)

Sources & evidence

ORD record
ord-2d43516d8cb6496fadf8c7441aab2121
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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