N,N-Dimethylpiperidin-4-amine → HCID 59468487, compound

HRID 1012192Notes

Reaction equation

HRID 1012192 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=O)[N:8]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CC(O)=O.CC(N(C)C)=O>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:21]=[CH:20][CH:19]=[C:16]([CH2:17][N:27]4[CH2:28][CH2:29][CH:24]([N:23]([CH3:30])[CH3:22])[CH2:25][CH2:26]4)[CH:15]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 59468578HCID 59468578, compound

Product 1

HCID 59468487HCID 59468487, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino]-benzaldehyde (25 mg, 0.069 mmol) and 4-dimethylaminopiperidine (13.3 mg, 0.104 mmol) in 25% HOAc in DMA was mixed for 2 h and then treated with MP-CNBH3 (2.5 eq.) for 18 h. The reactions were filtered and purified directly by LCMS to afford title compound (2.3 mg, 7%) for 2 steps. MS: m/z 472 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 1.37 (br q, J=11 Hz, 2H), 1.70 (br d, J=12 Hz, 2H), 1.94 (br t, J=11 Hz, 2H), 2.04 (br t, 1H), 2.87 (br d, J=11 Hz, 2H), 3.33 (s, 2H), 6.89 (d, J=7.5 Hz, 1H), 7.24 (t, J=7.5 Hz, 1H), 7.33 (dd, J=1, 5 Hz, 1H), 7.37 (m, 1H), 7.55 (br d, J=8 Hz, 1H), 7.86 (m, 1H), 7.89 (br s, 1H), 8.51 (dd, J=1.5, 5 Hz, 1H), 9.68 (s, 1H).

Workup

  1. additiontreated with MP-CNBH3 (2.5 eq.) for 18 h
  2. filtrationThe reactions were filtered
  3. custompurified directly by LCMS

Sources & evidence

ORD record
ord-1df82cca2a6f4cc1b02a1cfd21dbff7a
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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