Ethyl Bromide → HCID 58870816, compound

HRID 1927628Notes

Reaction equation

[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]([CH:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[NH:23][CH:24]=[CH:25][CH:26]=3)=[O:21])=[CH:15][C:14]=2[F:27])[CH2:9][CH2:8]1)=[O:5])[CH3:2].[CH3:36][C:37]([O-])(C)C.[Na+].C(Br)C>C1COCC1>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[N:23]([CH2:36][CH3:37])[CH:24]=[CH:25][CH:26]=3)=[O:21])=[CH:15][C:14]=2[F:27])[CH2:11][CH2:12]1)=[O:5])[CH3:35]

Participants

Conditions

Temperature: 25 °C

Procedure

To the solution of 1H-pyrrole-2-carboxylic acid {4-[4-(diethylcarbamoyl-phenyl-methyl)-piperidin-1-yl]-3-fluoro-phenyl}-amide (40 mg, 0.084 mmol) in THF (5 mL), NaOtBu (48 mg, 0.50 mmol) and ethyl bromide (54 mg, 0.50 mmol) was added. The mixture was stirred at 25° C. for 1 h and purified by PTLC to provide the title compound (27 mg, 42%). MS: 505.4. 1H NMR (CDCl3): 7.65 (s, 1H), 7.46 (dd, J=4.0, 2.4, 1H), 7.28-7.21 (m, 5H), 7.10-7.16 (m, 1H), 6.90-6.82 (m, 2H), 6.69-6.67 (m, 1H), 6.12 (dd, J=3.9, 2.6, 1H), 4.49 (dd, J=14.3, 6.8, 2H), 3.50-3.12 (m, 7H), 2.71-2.63 (m, 1H), 2.53-2.46 (m, 1H), 2.31-2.21 (m, 1H), 2.08-2.00 (m, 1H), 1.50-1.21 (m, 6H), 1.15-1.04 (m, 6H).

Workup

custompurified by PTLC

Sources & evidence

ORD record: ord-170a7ddcb2f04ff8af1fb6b6c20e630c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

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