Benzonitrile, 3-(bromomethyl)- → HCID 11703681, compound

HRID 1432162Notes

Reaction equation

HRID 1432162 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.Br[CH2:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26]>>[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]([CH2:21][C:22]4[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=4)[C:25]#[N:26])[CH2:17][CH2:18]3)[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 670930646-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine dihydrochloride

Product 1

HCID 11703681HCID 11703681, compound

Procedure

The title compound was prepared (282 mg, 75%) from 6-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine dihydrochloride (333 mg, 0.98 mmol) and 3-(bromomethyl)benzonitrile (191 mg, 0.98 mmol) by following the general procedure described for Preparation 12. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.68 (s, 1H), 7.57 (d, 2H), 7.43 (t, 1H), 7.00 (s, 1H), 4.88 (d, 1H), 4.20 (m, 1H), 3.56 (s, 2H), 2.85 (d, 2H), 2.25 (dt, 2H), 2.12 (d, 2H), 1.59 (m, 2H); MS (ESI) m/z: Calculated for C19H19ClN5S, 384.1; Observed: 384.2 (M++1).

Workup

  1. customdescribed for Preparation 12

Sources & evidence

ORD record
ord-129b287123e44b0e9d90d01bc7dd847c
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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