Methylamine → HCID 178485479, compound

HRID 572233Notes

Reaction equation

HRID 572233 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:29])[NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:6][CH:5]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:54][NH2:55]>C1COCC1>[CH3:54][NH:55][C:24](=[O:25])[C:23]1[CH:22]=[CH:21][C:20]([O:19][C@H:16]2[CH2:17][CH2:18][C@H:13]([NH:12][C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=3)=[O:29])[CH2:14][CH2:15]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522240HCID 178522240, compound

Product 1

HCID 178485479HCID 178485479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1728 (0.22 g, 0.5 mmol), EDC HCl (0.12 g, 0.63 mmol), HOBT (0.09 g, 0.63 mmol), TEA (0.17 mL, 0.63 mmol) in THF (10 mL) was added 2M MeNH2 in THF (1.25 mL, 2.5 mmol) at 0° C. The reaction mixture was allowed to slowly warm to room temperature overnight. The solvent was removed in vacuo and then purified by recrystallization with EtOAc/Hexanes gave the title compound, 0.16 g (71%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.53 (s, 1H), 8.28 (q, J=4 Hz, 1H), 7.77 (d, J=9 Hz, 2H), 7.47 (d, J=9 Hz, 2H), 7.22 (d, J=9 Hz, 2H), 6.99 (d, J=9 Hz, 2H), 6.21 (d, J=8 Hz, 1H), 4.49-4.36 (m, 1H), 3.62-3.45 (m, 1H), 2.75 (d, J=4 Hz, 3H), 2.11-1.87 (m, 4H), 1.57-1.25 (m, 4H).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by recrystallization with EtOAc/Hexanes

Sources & evidence

ORD record
ord-207cb42a9745407e9f8d3ae26ae5217b
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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