Tert-butyl 4-[3-(aminomethyl)phenoxy]piperidine-1-carboxylate → tert-Butyl 4-(3-{[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]methyl}phenoxy)piperidine-1-carboxylate

HRID 2239346Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.NC[C:24]1[CH:25]=[C:26]([CH:41]=[CH:42][CH:43]=1)[O:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([CH2:21][C:24]4[CH:25]=[C:26]([CH:41]=[CH:42][CH:43]=4)[O:27][CH:28]4[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:30][CH2:29]4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (522 mg, 1.62 mmol) and tert-butyl 4-[3-(aminomethyl)phenoxy]piperidine-1-carboxylate (544 mg, 1.78 mmol) were dissolved in MeOH (10 ml). The mixture was heated in a microwave for 30 minutes at 120° C. A precipitate was formed from MeOH. The precipitate was filtered off and washed with MeOH yielding the title compound as a white solid. Yield: 431 mg (48%). 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.63 (m, 2H), 7.47 (s, 1H), 7.43 (m, 2H), 7.30-7.25 (m, 1H), 6.95-6.91 (m, 2H), 6.86 (m, 1H), 5.19 (s, 2H), 4.46 (m, 1H), 3.67 (m, 2H), 3.33 (m, 2H), 1.94-1.85 (m, 2H), 1.77-1.67 (m, 2H), 1.54 (s, 9H).

Workup

filtrationThe precipitate was filtered off
washwashed with MeOH yielding the title compound as a white solid

Sources & evidence

ORD record: ord-f979507118614969ba1107c8181371ea
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723331B2

Reaction notes

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