Dimethylacetamide → HCID 178424911, compound

HRID 80854Notes

Reaction equation

HRID 80854 reaction equation
Cl[C:2]1[C:3]2[CH2:22][N:21]([C:23]3[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=3[CH3:32])[CH2:20][CH2:19][C:4]=2[N:5]=[C:6]([C:8]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10]([CH3:18])=[N:11][NH:12]3)[N:7]=1.C[CH2:34][N:35]([CH:39](C)C)[CH:36]([CH3:38])[CH3:37].CC([N:45](C)C)=O>>[CH3:14][C:13]1[C:9]2[C:10](=[CH:18][CH:15]=[C:16]([CH3:17])[C:8]=2[C:6]2[N:7]=[C:2]([N:45]3[CH2:38][CH:36]([N:35]([CH3:39])[CH3:34])[CH2:37]3)[C:3]3[CH2:22][N:21]([C:23]4[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=4[CH3:32])[CH2:20][CH2:19][C:4]=3[N:5]=2)[NH:11][N:12]=1

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 178424910HCID 178424910, compound

Product 1

HCID 178424911HCID 178424911, compound

Procedure

A solution of 4-chloro-2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (30 mg, 0.07 mmol), N,N-dimethylazetidin-3-amine bistrifluoroacetate salt (20.0 mg, 0.2 mmol) and DIEA (0.06 mL, 0.35 mmol) in DMA (1.5 mL) was heated to 180° C. for 3 min in a microwave reactor. The reaction mixture was filtered through a 0.45 μM PTFE filter and the filtrate was purified by reverse phase HPLC (C18, 10-100% acetonitrile-H2O with 0.1% NH4OH) to afford 1-(2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-N,N-dimethylazetidin-3-amine 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.43 (d, J=8.46 Hz, 1H), 7.30 (d, J=8.59 Hz, 1H), 7.13 (d, J=7.83 Hz, 1H), 7.04 (d, J=1.39 Hz, 1H), 6.91 (dd, J=1.52, 7.71 Hz, 1H), 4.36 (t, J=8.21 Hz, 2H), 4.08-4.20 (m, 4H), 3.32-3.38 (m, 2H), 3.18-3.27 (m, 1H), 2.79-2.97 (m, 3H), 2.31 (s, 3H), 2.27 (s, 3H), 2.18 (s, 6H), 2.04 (s, 3H), 1.24 (d, J=6.95 Hz, 6H); MS (ESL) m/z 510.5 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 μM PTFE
  2. filtrationfilter
  3. customthe filtrate was purified by reverse phase HPLC (C18, 10-100% acetonitrile-H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-463de6cb84ea45479461b874bd557fde
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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