2-Fluoro-5-formylbenzonitrile → 5-[[4-[(6-Chlorothieno[2,3-d]pyrimidin-4-yl)amino]-1-piperidinyl]methyl]-2-fluorobenzonitrile

HRID 1432163Notes

Reaction equation

HRID 1432163 reaction equation
Cl.Cl.[Cl:3][C:4]1[S:19][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:6]=2[CH:5]=1.[F:20][C:21]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][C:22]=1[C:23]#[N:24]>>[Cl:3][C:4]1[S:19][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][N:16]([CH2:29][C:26]4[CH:27]=[CH:28][C:21]([F:20])=[C:22]([CH:25]=4)[C:23]#[N:24])[CH2:17][CH2:18]3)[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 27695822-Fluoro-5-formylbenzonitrileHCID 670930646-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine dihydrochloride

Product 1

HCID 115022435-[[4-[(6-Chlorothieno[2,3-d]pyrimidin-4-yl)amino]-1-piperidinyl]methyl]-2-fluorobenzonitrile

Procedure

The title compound was prepared (392 mg, 41%) from 6-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine dihydrochloride (655 mg, 2.4 mmol) and 2-fluoro-5-formylbenzonitrile (399 mg, 2.7 mmol) by following the general procedure described for Preparation 11. 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 7.63 (m, 1H), 7.55 (m, 1H), 7.16 (m, 1H), 7.00 (s, 1H), 4.93 (d, 1H), 4.19 (m, 1H), 3.50 (s, 2H), 2.83 (d, 2H), 2.23 (dt, 2H), 2.10 (d, 2H), 1.59 (m, 2H); MS (ESI) m/z: Calculated for C19H18ClFN5S, 402.1; Observed: 402.2 (M++1).

Workup

  1. customdescribed for Preparation 11

Sources & evidence

ORD record
ord-9f665a65e15a4d1f81774b8b5ca43b92
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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