Morpholine → (2-Amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)-(5-bromothiophen-2-yl)-methanone

HRID 2086926Notes

Reaction equation

[C:1]([C:4]1[S:5][C:6](Br)=[CH:7][CH:8]=1)(=O)C.[Br:10][C:11]1[S:15][C:14]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:13][CH:12]=1.[CH2:21]([N:28]1CCC(=O)CC1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1CCOCC1.[S]>>[NH2:20][C:19]1[S:5][C:4]2[CH2:1][N:28]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:6][CH2:7][C:8]=2[C:18]=1[C:16]([C:14]1[S:15][C:11]([Br:10])=[CH:12][CH:13]=1)=[O:17]

Participants

Reactant 5

HCID 8083Morpholine

HCID 192201-Benzyl-4-piperidone

HCID 793352-Acetyl-5-bromothiophene

HCID 5362487Sulfur

HCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrile2×

Product 1

HCID 10181274(2-Amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)-(5-bromothiophen-2-yl)-methanoneYield 72%

Procedure

The procedure of Example 1 was followed except that 2-acetyl-5-bromothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-bromothiophene-2-carbonyl)acetonitrile (Steps A and B). 1-Benzyl-4-piperidone (van der Klein et al., (1999), J. Med. Chem. 42: 3629-3635), 2-(5-bromothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 72%; IR (KBr) cm−1: 3411, 2923, 1570, 1411, 1314, 978; 1H NMR (CDCl3):δ2.38 (t, J=5.4 Hz, 2H), 2.59 (t, 2H, J=5.4 Hz), 3.48 (s, 2H), 3.67 (s, 2H), 6.28 (bs, 2H), 7.01 (d, 1H, J=4 Hz), 7.15 (d, 1H, J=4 Hz), 7.32 (m, 5H); brown solid, mp: 87-89° C. (petroleum ether).

Sources & evidence

ORD record: ord-cb10444204424d15bae8faec66c0597e
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727258B2

Reaction notes

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