2-(3-Fluorophenyl)ethanamine → HCID 59263921, compound

HRID 644978Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[C:11]([N:15]([CH:42]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[CH2:16][CH2:17][N:18]([CH2:29][CH2:30][C:31]1[C:39]2[S:38][C:37](=[O:40])[NH:36][C:35]=2[C:34]([OH:41])=[CH:33][CH:32]=1)[C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:14])[CH:12]=[CH2:13]>C(O)C>[CH:42]1([N:15]([C:11](=[O:14])[CH2:12][CH2:13][NH:10][CH2:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:16][CH2:17][N:18]([CH2:29][CH2:30][C:31]2[C:39]3[S:38][C:37](=[O:40])[NH:36][C:35]=3[C:34]([OH:41])=[CH:33][CH:32]=2)[C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

Conditions

Temperature: 50 °C

Procedure

2-(3-Fluorophenyl)ethanamine (0.573 mL) was added to benzyl {2-[acryloyl(cycloheptyl)amino]ethyl}[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]carbamate, prepared as in Example 23 step ii), (0.786 g) in ethanol (15 mL). The resulting solution was stirred at 50° C. for 32 h. The volatiles were removed in vacuo and the crude material was purified by flash silica chromatography, elution gradient 0.5:0.5:19 to 1:7:13 7M NH3 in methanol:ethanol:ethyl acetate. Pure fractions were evaporated to dryness to afford the sub-title product (0.759 g) as a pale yellow foam.

Workup

customThe volatiles were removed in vacuo
customthe crude material was purified by flash silica chromatography, elution gradient 0.5:0.5:19 to 1:7:13 7M NH3 in methanol
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-42ceb4cf96ea47c19ace8a47a9088d92
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700782B2

Reaction notes

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