Trifluoroacetic acid → Trifluoroacetic acid

HRID 340125Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[C:36]4[CH:43]([CH3:44])[CH2:42][CH2:41][C:37]=4[N:38]=[CH:39][N:40]=3)=[CH:31][CH:30]=2)[CH2:16][N:17]([CH:25]([CH3:27])[CH3:26])C(=O)OC(C)(C)C)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[C:36]4[CH:43]([CH3:44])[CH2:42][CH2:41][C:37]=4[N:38]=[CH:39][N:40]=3)=[CH:31][CH:30]=2)[CH2:16][NH:17][CH:25]([CH3:27])[CH3:26])=[CH:11][CH:10]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (0.5 mL) was added dropwise to a solution of (R)-tert-butyl 2-(4-chlorophenyl)-2-(4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)phenoxy)ethyl(isopropyl)carbamate (26 mg, 0.0498 mmol) in methylene chloride (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then at room temperature for 2 hours. The contents were concentrated. The resulting residue was purified by reverse-phase HPLC to give (R)-N-(2-(4-chlorophenyl)-2-(4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)phenoxy)ethyl)propan-2-amine as TFA salt (7.5 mg, 23%). 1H NMR (d6-DMSO, 500 MHz) δ□(ppm): 8.9 (s, 1H), 8.7 (s, br, 2H), 7.8 (t, 2H), 7.5 (m, 4H), 7.1 (d, 2H), 5.7 (d, 1H), 3.8 (m, 1H), 3.4-3.5 (m, 2H), 3.3-3.4 (m, 1H), 3.0-3.1 (m, 1H), 2.9 (m, 1H), 2.3 (m, 1H), 1.7 (m, 1H), 1.3 (dd, 6H), 0.9 (dd, 3H). MS (422.3, M+1).

Workup

waitat room temperature for 2 hours
concentrationThe contents were concentrated
customThe resulting residue was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-27055fb3efb34badb020af86cd05a54d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895566B2

Reaction notes

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