Cyclopropanemethanamine → HCID 90466704, compound

HRID 1753234Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[C:12]([C:20](O)=[O:21])=[CH:11]2)[C:4]=1[CH3:23].[CH:24]1([CH2:27][NH2:28])[CH2:26][CH2:25]1>>[CH:24]1([CH2:27][NH:28][C:20]([C:12]2[C:13]3=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=[C:18]3[N:10]([CH2:9][C:5]3[C:4]([CH3:23])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=3)[CH:11]=2)=[O:21])[CH2:26][CH2:25]1

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 117819025HCID 117819025, compound

Product 1

HCID 90466704HCID 90466704, compound

Procedure

See FIG. 18(b). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.100 g, 0.32 mmol) and cyclopropylmethanamine (0.046 g, 0.64 mmol), TEA (0.134 mL, 0.96 mmol) was added. After 3 min1-Propanephosphonic acid cyclic anhydride (0.255 g, 0.80 mmol) was added. The resulting reaction mixture was stirred at rt for 50 min. LCMS analysis showed formation of required product. Reaction was diluted with DCM and water. DCM layer was extracted and washed with brine and dried over sodium sulphate and concentrated. Purification was done on Waters RP system to get product N-(cyclopropylmethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.045 g, 38.5%). ES+MS m/z: 366.44. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.21-0.33 (m, 2H ) 0.41-0.56 (m, 2 H ) 1.08 (m, J=6.97 Hz, 1 H ) 2.24 (s, 3 H ) 2.40 (s, 3 H ) 3.26 (d., 2 H ) 3.94 (s, 3 H ) 5.63 (s, 2 H ) 7.75 (s, 1 H ) 8.11 (s, 1 H) 8.35 (s, 1 H ) 8.42 (s, 1H ) 8.74 (t, J=5.65 Hz, 1 H ).

Workup

customThe resulting reaction mixture

Sources & evidence

ORD record: ord-ca7539bc25ae497493fe3b6abc97baaf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163020B2

Reaction notes

Loading…