Ethyl isocyanate → HCID 67441845, compound

HRID 1400942Notes

Reaction equation

HRID 1400942 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([C:19]3[S:27][C:26]4[C:21](=[N:22][CH:23]=[CH:24][C:25]=4[O:28][C:29]4[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][CH:39]5[CH2:41][CH2:40]5)=[O:37])=[CH:31][C:30]=4[F:42])[CH:20]=3)=[CH:17][CH:18]=2)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[CH2:43]([N:45]=[C:46]=[O:47])[CH3:44]>C1COCC1>[CH:39]1([NH:38][C:36](=[O:37])[NH:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][C:25]3[CH:24]=[CH:23][N:22]=[C:21]4[CH:20]=[C:19]([C:16]5[N:15]=[CH:14][C:13]([CH2:12][N:5]([CH:3]6[CH2:2][N:1]([C:46](=[O:47])[NH:45][CH2:43][CH3:44])[CH2:4]6)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:18][CH:17]=5)[S:27][C:26]=34)=[C:30]([F:42])[CH:31]=2)[CH2:40][CH2:41]1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 68223921HCID 68223921, compound

Product 1

HCID 67441845HCID 67441845, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 432 (0.135 mmol) in THF (5 mL) were added TEA (0.094 mL, 0.675 mmol) and ethyl isocyanate (0.032 mL, 0.405 mmol) and stirred at RT for 1 h. The mixture was then concentrated, water was added to form a precipitate that was collected by filtration, rinsed with water, air-dried to afford the title compound 433 (78 mg, 88% yield for 2 steps) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.71 (s, 1H), 8.55 (d, J=1.6 Hz, 1H), 8.52 (d, J=5.6 Hz, 1H), 8.34 (s, 1H), 8.25 (d, J=8.4 Hz, 1H), 7.88 (dd, J=8.0, 2.0 Hz, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 6.65 (dd, J=5.6, 0.8 Hz, 1H), 6.57 (bd, J=2.8 Hz, 1H), 6.27 (t, J=5.6 Hz, 1H), 4.06 (q, J=7.2 Hz, 2H), 3.84-3.75 (m, 5H), 3.69-3.61 (m, 2H), 3.02-2.94 (m, 2H), 2.59-2.51 (m, 1H), 1.18 (t, J=7.2 Hz, 3H), 0.97 (t, J=7.2 Hz, 3H), 0.68-0.62 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 662.60 (M+H).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionwater was added
  3. customto form a precipitate that
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. customair-dried

Sources & evidence

ORD record
ord-4548443ca9c244fcbc2ba3dc3717ad78
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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