Nicotinamide → HCID 14986521, compound

HRID 1975071Notes

Reaction equation

Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1O.[C:14]([NH2:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.[K+].[Br-].C[O:26]C1C=CSC=1>>[OH:26][CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1[NH:22][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1

Participants

Reactant 4

HCID 936Nicotinamide

HCID 1402493-Methoxythiophene

HCID 253877Potassium Bromide

HCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 14986521HCID 14986521, compound

Procedure

The title compound was prepared as described for Example 3 starting with 6-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H -thieno[3,2-b]pyran (4.0 g, 15.2 mmol) and nicotinamide (3.7 g, 30.4 mmol) to give 1.1 g (24%): m.p. 248°-49° C.; IR (KBr): 3329, 3312,1648, 1594, 1569 cm-1 ; MS: m/z 305 (MH+); 1 1H NMR (CDCl3) 6 9.02 (s, 1H), 8.79 (d, J=5,6 Hz, 1H), 8.14 (d, J=5,6 Hz, 1H), 7.44 (m, 1H), 7.18 (d, J=5.4 Hz, 1H), 6.64 (d, J=5.4 Hz, 1H), 6.55 (d, J=5,6, 1H), 5.20 (m, 1H), 4.46 (brs, 1H), 3.81 (d, J=9.4 Hz, 1H), 1.50 (s, 3H), 1.36 (s, 3H).

Workup

customto give 1.1 g (24%)

Sources & evidence

ORD record: ord-17a2d55af877497ca73fbc80498cd11c
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284857

Reaction notes

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