Cyclopropylamine → HCID 67441535, compound

HRID 1400911Notes

Reaction equation

HRID 1400911 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:19]3[N:20]([CH3:31])[C:21]([CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:22][N:23]=3)[S:18][C:11]=12)[NH2:5].CC[N:34]([CH:38]([CH3:40])[CH3:39])[CH:35](C)C.ClC(Cl)([O:44]C(=O)OC(Cl)(Cl)Cl)Cl.C1(N)CC1>C1COCC1>[CH:38]1([NH:34][C:35]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[CH:16]=[C:17]([C:19]5[N:20]([CH3:31])[C:21]([CH2:24][N:25]6[CH2:30][CH2:29][O:28][CH2:27][CH2:26]6)=[CH:22][N:23]=5)[S:18][C:11]=34)=[C:2]([F:1])[CH:3]=2)=[O:44])[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58474478HCID 58474478, compound

Product 1

HCID 67441535HCID 67441535, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of aniline 297 (200 mg, 0.455 mmol) in THF (20 mL) at 0° C. was added DIPEA (0.318 mL, 1.820 mmol) and triphosgene (81 mg, 0.273 mmol). The mixture was stirred at 0° C. for 1 hr before cyclopropylamine (0.160 mL, 2.275 mmol) was added, and was allowed to warm to RT over 1 hr. The mixture was concentrated and purified by Biotage (MeOH/DCM, 0-22%, SNAP 25 g cartridge) to afford title compound 298 (54 mg, 0.103 mmol, 22.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.50 (d, 1H, J=5.5 Hz), 7.89 (s, 1H), 7.70 (dd, 1H, J1=2.3 Hz, J2=13.9 Hz), 7.35 (t, 1H, J=9.0 Hz), 7.18-7.16 (m, 1H), 6.96 (s, 1H), 6.65 (d, 1H, J=5.5 Hz), 6.55-6.54 (m, 1H), 3.91 (s, 3H), 3.55 (t, 4H, J=3.4 Hz), 3.51 (s, 2H), 2.54-2.51 (m, 1H), 2.37 (m, 4H), 0.65-0.61 (m, 2H), 0.42-0.38 (m, 2H). MS: 523.6 (MH)+

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. custompurified by Biotage (MeOH/DCM, 0-22%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-031e6a2c947643659b929a54ef3d6332
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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