Phosgene → HCID 57563036, compound

HRID 1726210Notes

Reaction equation

HRID 1726210 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]#[N:38])[CH:32]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:27])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:39](Cl)(Cl)=[O:40].[Cl-].[NH4+].CC[N:47](C(C)C)C(C)C>C1(C)C=CC=CC=1>[C:37]([C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][N:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:39]([NH2:47])=[O:40])=[CH:3][CH:4]=1)[CH:9]1[CH2:10][CH2:11][N:12]([CH:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19](=[O:28])[C:20]2[C:21]([CH3:27])=[CH:22][CH:23]=[CH:24][C:25]=2[CH3:26])[CH2:13][CH2:14]1)#[N:38]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 57563039HCID 57563039, compound

Product 1

HCID 57563036HCID 57563036, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of COMPOUND 142 (61 mg, 0.12 mmol) in toluene (1 mL) was added phosgene (20% in toluene, 82 μL, 0.15 mmol) and the resultant slurry was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in DMF (1 mL). To the solution were added ammonium chloride (33 mg, 0.62 mmol) and DIPEA (120 μL, 0.69 mmol) and the mixture was stirred at room temperature for 17 hours to afford COMPOUND 158 as a white solid (24 mg, 36%) following work-up and purification. 1H NMR (CDCl3) δ 1.00-1.15 (m, 5H), 1.55 (m, 1H), 1.71 (m, 3H), 2.16 (m, 1H), 2.30 (s, 6H), 2.56 (m, 1H), 2.75-2.87 (m, 3H), 3.29 (m, 1H), 3.57 (m, 1H), 3.79-3.90 (m, 3H), 4.63 (s, 2H), 6.41 (s, 1H), 6.50 (d, 2H, J=7.8 Hz), 6.92-7.04 (m, 5H), 7.43 (s, 3H), 7.52 (br s, 1H), 8.38 (br s, 1H). 13C NMR (CDCl3) δ 13.81, 19.54, 29.41, 30.68, 31.30, 40.24, 43.99, 48.69, 52.49, 57.30, 60.85, 112.86, 114.97, 119.39, 125.05, 127.70, 128.84, 129.63, 130.41, 130.90, 131.39, 134.47, 138.87, 142.42, 146.09, 158.05, 170.39. ES-MS m/z 553 (M+H). Anal. Calcd. for C33H40N6O2.0.85CH2Cl2.0.1C6H14: C, 65.31; H, 6.86; N, 13.27. Found. C, 65.38; H, 6.66; N, 13.07.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (1 mL)
  3. stirringthe mixture was stirred at room temperature for 17 hours

Sources & evidence

ORD record
ord-6c10513d77254dce88cdaa03e9999d16
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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