Dimethylformamide → HCID 67442954, compound

HRID 1400937Notes

Reaction equation

HRID 1400937 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:23][C:22]4[C:17](=[N:18][CH:19]=[CH:20][C:21]=4[O:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:34][CH:35]5[CH2:37][CH2:36]5)=[O:33])=[CH:27][C:26]=4[F:38])[CH:16]=3)=[N:13][CH:14]=2)[CH2:4][CH2:3]1.[CH2:39]([O:41][C:42]([CH2:44][N:45]=[C:46]=[O:47])=[O:43])[CH3:40].CN(C=O)C>C1COCC1>[CH:35]1([NH:34][C:32](=[O:33])[NH:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][C:21]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:16]=[C:15]([C:12]5[N:13]=[CH:14][C:9]([CH2:8][N:5]6[CH2:6][CH2:7][CH:2]([NH:1][C:46](=[O:47])[NH:45][CH2:44][C:42]([O:41][CH2:39][CH3:40])=[O:43])[CH2:3][CH2:4]6)=[CH:10][CH:11]=5)[S:23][C:22]=34)=[C:26]([F:38])[CH:27]=2)[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76283Ethyl isocyanatoacetateHCID 67443027HCID 67443027, compound

Product 1

HCID 67442954HCID 67442954, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 343 (106 mg, 0.20 mmol, scheme 71) in THF (3 mL) was added ethoxycarbonylmethyl isocyanate (0.068 mL, 0.6 mmol) and stirred at RT for 3 h. To the mixture was added DMF (2 mL) and stirred for 1 h. The mixture was then concentrated, water was added to form a precipitate that was collected by filtration, rinsed with water and purified via Biotage [linear gradient 2-20%, (methanol/dichloromethane; SiliaFlash 10 g cartridge]. Title compound 425 was obtained as a white solid (79.5 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.73 (s, 1H), 8.54 (brd, 1H), 8.52 (d, J=5.6 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.85 (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), 7.23-7.18 (m, 1H), 6.64 (d, J=5.2 Hz, 1H), 6.59 (bd, 1H), 6.15 (d, J=8.0 Hz, 1H), 6.06 (t, J=8.0 Hz, 1H), 4.06 (q, J=6.4 Hz, 2H), 3.74 (d, J=6.50 Hz, 2H), 3.54 (s, 2H), 2.77-2.66 (m, 2H), 2.58-2.51 (m, 2H), 2.13-2.04 (m, 2H), 1.78-1.70 (m, 2H), 1.40-1.30 (m, 2H), 1.18 (t, J=6.8 Hz, 3H), 0.68-0.62 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 662.28 (M+H).

Workup

  1. stirringstirred for 1 h
  2. concentrationThe mixture was then concentrated
  3. additionwater was added
  4. customto form a precipitate that
  5. filtrationwas collected by filtration
  6. washrinsed with water
  7. custompurified via Biotage [linear gradient 2-20%

Sources & evidence

ORD record
ord-54135311f0644da2b44bfb067baabe73
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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