N,N-Dimethyl-1,3-propanediamine → HCID 49770158, compound

HRID 1157765Notes

Reaction equation

HRID 1157765 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=O)[N:10]([CH3:18])[N:9]=2)=[C:4]2[NH:19][CH:20]=[C:21]([C:22](=[O:42])[C:23](=[O:41])[N:24]3[CH2:29][CH2:28][N:27]([C:30]4[N:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:33]=[N:32][N:31]=4)[CH2:26][CH2:25]3)[C:3]=12.[CH3:43][N:44]([CH3:49])[CH2:45][CH2:46][CH2:47][NH2:48]>CN(C=O)C>[CH3:43][N:44]([CH3:49])[CH2:45][CH2:46][CH2:47][NH:48][C:13]([C:11]1[N:10]([CH3:18])[N:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([F:1])=[C:3]3[C:21]([C:22](=[O:42])[C:23](=[O:41])[N:24]4[CH2:29][CH2:28][N:27]([C:30]5[N:34]([C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=6)[N:33]=[N:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:20][NH:19][C:4]=23)[CH:12]=1)=[O:15]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 49770155HCID 49770155, compound

Product 1

HCID 49770158HCID 49770158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a sealable flask containing ethyl 3-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxylate (0.058 g, 0.10 mmol) was added N1,N1-dimethylpropane-1,3-diamine (0.7 mL). The mixture was sealed and heated to 50° C. for 20.5 h. The mixture was cooled to rt, and was diluted with DMF and was passed through a plug of celite to remove any solids. The DMF solution was purified by prep HPLC to give N-(3-(dimethylamino)propyl)-3-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide.TFA. (0.020 g) as an off-white solid. LCMS: m/e 629.5 (M+H)+, ret time 1.93 min (method 2). 1H NMR (500 MHz, MeOD) δ ppm 8.75 (s, 1H) 8.61 (s, 1H) 7.97-8.11 (m, 5H) 7.79 (s, 1H) 4.69 (s, 3H) 4.21-4.25 (m, 2H) 4.01-4.04 (m, 2H) 3.91 (t, J=6.26 Hz, 2H) 3.76-3.82 (m, J=3.66 Hz, 2H) 3.65-3.75 (m, 10H) 2.45-2.52 (m, 2H).

Workup

  1. customThe mixture was sealed
  2. temperatureThe mixture was cooled to rt
  3. customto remove any solids
  4. customThe DMF solution was purified by prep HPLC

Sources & evidence

ORD record
ord-632fde3fd4b547ae94caba83e256a5dc
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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