2-(4-Bromo-thiophen-2-yl)-tetrahydro-furan-3-carbonitrile → 4-Amino-2-[5-(3-cyano-tetrahydro-furan-2-yl)-thiophen-3-yl]-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1868321Notes

Reaction equation

HRID 1868321 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]2[CH:11]([C:12]#[N:13])[CH2:10][CH2:9][O:8]2)[S:5][CH:6]=1.[NH2:14][C:15]1[C:20]2[CH:21]=[C:22](Br)[S:23][C:19]=2[C:18]([C:25]([NH2:27])=[O:26])=[CH:17][N:16]=1>>[NH2:14][C:15]1[C:20]2[CH:21]=[C:22]([C:2]3[CH:3]=[C:4]([CH:7]4[CH:11]([C:12]#[N:13])[CH2:10][CH2:9][O:8]4)[S:5][CH:6]=3)[S:23][C:19]=2[C:18]([C:25]([NH2:27])=[O:26])=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 184465132-(4-Bromo-thiophen-2-yl)-tetrahydro-furan-3-carbonitrileHCID 588407134-Amino-2-Bromothieno[3,2-C]pyridine-7-Carboxamide

Product 1

HCID 690658254-Amino-2-[5-(3-cyano-tetrahydro-furan-2-yl)-thiophen-3-yl]-thieno[3,2-c]pyridine-7-carboxylic acid amide

Procedure

87 was prepared from 2-(4-bromo-thiophen-2-yl)-tetrahydro-furan-3-carbonitrile 86 and 4-amino-2-bromo-thieno[3,2-c]pyridine-7-carboxylic acid amide 17 in a similar manner to that described in Example 18. 1H NMR (400 MHz, d6-DMSO) δ: 8.48 (s, 1H), 7.90 (bs, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.46 (s, 1H), 7.26 (bs, 1H), 7.12 (s, 2H), 5.30 (d, J=7.49 Hz, 1H), 4.09 (m, 1H), 3.99 (m, 1H), 3.44 (m, 1H), 2.49 (m, 1H), 2.33 (m, 1H). MS (EI) m/z (M+H+) 371.

Sources & evidence

ORD record
ord-8455c5d06c2f42e3941c139ba1a25669
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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