Cyclopropylamine → HCID 67443701, compound

HRID 1400833Notes

Reaction equation

HRID 1400833 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[N:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][O:26][CH2:25][C:24]5=[O:29])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:32])[CH:3]=1.ClC(Cl)(O[C:37](=[O:43])OC(Cl)(Cl)Cl)Cl.[CH:45]1([NH2:48])[CH2:47][CH2:46]1>C1COCC1.C(Cl)Cl>[CH:45]1([NH:48][C:37]([NH:1][C:2]2[CH:31]=[CH:30][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[CH:13]=[C:14]([C:16]5[CH:17]=[CH:18][C:19]([CH2:22][N:23]6[CH2:28][CH2:27][O:26][CH2:25][C:24]6=[O:29])=[CH:20][N:21]=5)[S:15][C:8]=34)=[C:4]([F:32])[CH:3]=2)=[O:43])[CH2:47][CH2:46]1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 94429TriphosgeneHCID 58474436HCID 58474436, compound

Product 1

HCID 67443701HCID 67443701, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 122 (65 mg, 0.144 mmol) in THF (7 mL) was added TEA (0.06 mL, 0.433 mmol) and triphosgene (42.8 mg, 0.144 mmol) in THF (2 mL) and the mixture was stirred at RT for an hour. Cyclopropylamine (16.48 mg, 0.289 mmol) was added and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM and washed with saturated NH4Cl solution. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with acetone to afford title compound 123 (18 mg, 23% yield) as an olive colored solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.55 (s, 1H), 8.51 (d, J=5.48 Hz, 1H), 8.34 (s, 1H), 8.25 (d, J=8.22 Hz, 1H), 7.82 (m, 1H), 7.71 (m, 1H), 7.36 (t, J=8.99 Hz, 1H), 7.19 (m, 1H), 6.63 (d, J=5.48 Hz, 1H), 6.55 (s, 1H), 4.60 (s, 2H), 4.12 (s, 2H), 3.83 (m, 2H), 3.36 (m, 2H), 2.49 (m, 1H), 0.64 (m, 2H), 0.42 (m, 2H). MS (m/z)=534.51 (M+H)

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. washwashed with saturated NH4Cl solution
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was triturated with acetone

Sources & evidence

ORD record
ord-f32a195e74a349dc8749ad8893037179
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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