2-(3-Fluorophenyl)ethanamine → HCID 58603368, compound

HRID 14970Notes

Reaction equation

HRID 14970 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([S:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@@H:18]3[CH3:30])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[F:31][C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][NH2:40])[CH:35]=[CH:36][CH:37]=1>>[F:31][C:32]1[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=1)[CH2:38][CH2:39][NH:40][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[CH3:30])(=[O:15])=[O:16])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 86603331HCID 86603331, compound

Product 1

HCID 58603368HCID 58603368, compound

Procedure

Intermediate 153 from above was coupled with 2-(3-fluorophenyl)ethanamine following procedure F. The product was deprotected by procedure G2. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, MeOD-d6, shifts relative to the solvent peak at 3.31 ppm) δ 8.6 (d, 1H) 8.5 (d, 1H) 8.4 (d, 1H), 8.1 (d, 1H), 7.8 (t, 1H), 7.6 (d, 1H), 7.2 (t, 1H), 7.1 (d, 1H), 7.0 (d, 1H), 6.8 (d, 1H), 3.9 (m, 3H), 3.4 (m, 1H), 3.3 (m, 2H), 3.2 (m, 2H), 3.1 (m, 1H), 3.0 (t, 2H), 1.2 (d, 3H).

Sources & evidence

ORD record
ord-c99ae1ee287f4b08a46c2ffa7a5697e7
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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