2-Acetylthiophene → HCID 10155061, compound

HRID 2086935Notes

Reaction equation

[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([CH2:16][C:17]#[N:18])=[O:15].[CH2:19](C1CCC(=O)CC1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:5][C:6]2[CH2:2][CH:1]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:4][CH2:8][C:7]=2[C:16]=1[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)=[O:15]

Participants

Reactant 5

HCID 69202-Acetylthiophene

HCID 8083Morpholine

HCID 1418532-Thenoylacetonitrile2×

HCID 5362487Sulfur

HCID 106552354-Benzylcyclohexanone

Product 1

HCID 10155061HCID 10155061, compoundYield 72%

Procedure

The procedure of Example 1 was followed except that 2-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophen-2-carbonyl)acetonitrile (Steps A and B). 4-Benzyl-cyclohexanone (Rosowsky etal., (1999) J. Med. Chem. 42: 1007-1017), 2-(thiophen-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: 3465, 2925, 1554, 1425, 1270, 1041, 768, 730, 702; 1H NMR (CDCl3):□ 0.88 (m, 1H), 1.27 (m, 2H, 1.56 (m, 1H), 2.23 (m, 3H), 2.66 (dd, 2H, J=7.2 and 3 Hz), 6.11 (bs, 2H), 7.04 (t, 1 H, J=4.4 Hz), 7.23 (m, 6H), 7.52 (d, 1H, J=4.8 Hz); mp: 116-118° C. (petroleum ether).

Sources & evidence

ORD record: ord-acdb5d3b7eab49ac972f9d3b73c4651f
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727258B2

Reaction notes

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