Hydrochloric Acid → HCID 66846170, compound

HRID 1916429Notes

Reaction equation

HRID 1916429 reaction equation
[ClH:1].O1CCOCC1.[Cl:8][C:9]1[CH:10]=[C:11]([C@@H:15]([C@H:35]2[N:39](C(OC(C)(C)C)=O)[C:38]([CH3:48])([CH3:47])[CH2:37][CH2:36]2)[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:25]4[C@H:32]([CH3:33])[CH2:31][C@@H:30]([OH:34])[C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:20][CH2:19]2)=[O:17])[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[ClH:8].[ClH:1].[Cl:8][C:9]1[CH:10]=[C:11]([C@@H:15]([C@@H:35]2[CH2:36][CH2:37][C:38]([CH3:47])([CH3:48])[NH:39]2)[C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[C:25]4[C@H:32]([CH3:33])[CH2:31][C@@H:30]([OH:34])[C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:22][CH2:23]2)=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66846260HCID 66846260, compound

Product 1

HCID 66846170HCID 66846170, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4M HCl in dioxane (6 mL, 24 mmol) was added to a solution of (S)-tert-butyl 5-((S)-1-(3-chlorophenyl)-2-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (0.020 g, 0.034 mmol) in dry DCM (15 mL) and stirred overnight. The solvent was evaporated to dryness to reveal (S)-2-(3-chlorophenyl)-2-((S)-5,5-dimethylpyrrolidin-2-yl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)ethanone dihydrochloride (0.015 g, 0.027 mmol, 79% yield). HPLC, 220 nm, retention time=1.91 minutes, 92% purity. LC/MS, retention time=2.15 minutes, (APCI+) m/z=484 [M+H]+. 1H NMR (400 MHz, D2O) 8.35 (s, 1H), 7.35-7.28 (m, 3H), 7.25-7.15 (m, 1H), 5.22 (t, J=8.20 Hz, 1H), 4.28-4.00 (m, 2H), 3.88-3.71 (m, 1H), 3.67-3.55 (m, 1H), 3.55-3.42 (m, 4H), 3.36-3.05 (m, 1H), 2.16 (dd, J1=7.81 Hz, J2=13.27 Hz, 1H), 2.10-1.93 (m, 1H), 1.88-1.70 (m, 4H), 1.36 (s, 3H), 1.30 (s, 3H), 0.94 (d, J=7.03 Hz, 3H).

Workup

  1. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-89f9ee7bc42a483abd895644f8200a8a
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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