Cyclopropanemethanamine → HCID 72792837, compound

HRID 1753256Notes

Reaction equation

HRID 1753256 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14](O)=[O:15])=[CH:6]1.[CH:23]1([CH2:26][NH2:27])[CH2:25][CH2:24]1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[CH:23]1([CH2:26][NH:27][C:14]([C:7]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:13]3[N:5]([CH2:4][C:3]3[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[CH:20][C:2]=3[F:1])[CH:6]=2)=[O:15])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 111923Propylphosphonic anhydrideHCID 117818900HCID 117818900, compound

Product 1

HCID 72792837HCID 72792837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 24(c). In a 50 mL round-bottomed flask 1-(2-fluoro-6-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.130 g, 0.43 mmol), cyclopropylmethanamine (0.040 g, 0.56 mmol) and TEA (0.181 mL, 1.30 mmol) was taken DCM (10 mL) under N2. To this 1-Propanephosphonic acid cyclic anhydride (0.317 g, 1.00 mmol) was added. The resulting reaction 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-(2-fluoro-6-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.060 g, 39.2%). ES+MS m/z: 354 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.24 (q, J=4.90 Hz, 2 H ) 0.38-0.50 (m, 2 H ) 1.03 (t, J=7.06 Hz, 1H ) 3.25 (t, J=6.22 Hz, 2 H) 3.88 (s, 3 H ) 5.47 (s, 2 H ) 6.83-6.99 (m, 2 H ) 7.26-7.46 (m, 2 H ) 8.02 (s, 1H ) 8.07 (d, J=8.10 Hz, 1 H ) 8.49 (d, J=3.96 Hz, 1 H ) 8.75 (t, J=5.65 Hz, 1 H ).

Workup

  1. customThe resulting reaction

Sources & evidence

ORD record
ord-2df22313396641a6abf2678dd3b596fb
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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