1-[(3,5-Difluorophenyl)methyl]piperidin-4-amine → N-(1-(3,5-Difluorobenzyl)piperidin-4-yl)-6-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 1432175Notes

Reaction equation

HRID 1432175 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[C:9]([Cl:18])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1>>[F:19][C:20]1[CH:21]=[C:22]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:23][N:24]1[CH2:25][CH2:26][CH:27]([NH:30][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=4)=[C:9]([Cl:18])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 221824001-[(3,5-Difluorophenyl)methyl]piperidin-4-amineHCID 579331454,6-Dichloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine

Product 1

HCID 11670347N-(1-(3,5-Difluorobenzyl)piperidin-4-yl)-6-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine

Procedure

The title compound was prepared (140 mg, 49%) from 4,6-dichloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (175 mg, 0.59 mmol) and 1-(3,5-difluorobenzyl)piperidin-4-amine (170 mg, 0.7 mmol) by following the general procedure described for Preparation 6. 1H NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 7.45 (m, 2H), 7.30 (m, 2H), 6.85 (m, 2H), 6.65 (m, 1H), 4.65 (m, 1H), 4.05 (bs, 1H), 3.40 (s, 2H), 2.40 (m, 2H), 2.15 (m, 2H), 1.85 (m, 2H), 1.15 (m, 1H). MS (ESI) m/z: Calculated: 488.1; Observed: 489.2 (M++1).

Workup

  1. customdescribed for Preparation 6

Sources & evidence

ORD record
ord-2152246441424d8eb2004fd4fe334c4b
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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