1-Benzothiophene-3-carbaldehyde → 6-(Morpholino)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one

HRID 1468800Notes

Reaction equation

HRID 1468800 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:16])=[C:11]([CH:15]=2)[C:12]([NH2:14])=[O:13])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:17]1[CH:22]=[C:21]2[C:23]([CH:26]=O)=[CH:24][S:25][C:20]2=[CH:19][CH:18]=1>>[O:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:15]=[C:11]3[C:10](=[CH:9][CH:8]=2)[N:16]=[C:26]([C:23]2[C:21]4[CH:22]=[CH:17][CH:18]=[CH:19][C:20]=4[S:25][CH:24]=2)[NH:14][C:12]3=[O:13])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 2273281-Benzothiophene-3-carbaldehydeHCID 105609362-Amino-5-(morpholin-4-yl)benzamide

Product 1

HCID 1362721706-(Morpholino)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one

Procedure

Compound 31 was synthesized from 5-morpholinyl-2-aminobenzamide (13) (1.6 g, 7.3 mmol) and thianaphthene-3-carboxaldehyde (16) (1.2 g, 7.3 mmol): yield 1.6 g (60%); brown crystals; mp>300° C.; 1H NMR (DMSO-d6) δ 2.47 (4H, t, J=4.7 Hz, CH2NCH2), 3.75 (4H, t, J=4.7 Hz, CH2OCH2), 7.44-7.59 (4H, m, 4×ArH), 7.67-7.72 (1H, m, 1×ArH), 8.03-8.07 (1H, m, 1×ArH), 8.67 (1H, s, 1×ArH), 8.96-9.00 (1H, m, 1×ArH), 12.31 (1H, br s, NH) ppm; MS (ESI) m/z 363; Anal. (C20H17N3O2S): C, H, N.

Sources & evidence

ORD record
ord-6c0be82682654eb1a088a10725579889
Source dataset
uspto-grants-2015_04
Patent number
US09006239B2

Reaction notes

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