Phenyl isocyanate → HCID 69087691, compound

HRID 1047084Notes

Reaction equation

HRID 1047084 reaction equation
CCN(CC)CC.[C:8]1([N:14]=[C:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[C:26]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[NH:30][C:29]4[N:37]=[CH:38][CH:39]=[CH:40][C:28]=4[N:27]3[C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([C:48]3([NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])[CH2:51][CH2:50][CH2:49]3)=[CH:44][CH:43]=2)=[CH:20][CH:19]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH:14]([C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:25]=[C:26]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[NH:30][C:29]4[N:37]=[CH:38][CH:39]=[CH:40][C:28]=4[N:27]3[C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([C:48]3([NH:52][C:53](=[O:59])[O:54][C:55]([CH3:57])([CH3:56])[CH3:58])[CH2:49][CH2:50][CH2:51]3)=[CH:44][CH:43]=2)=[CH:22][CH:23]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 69087658HCID 69087658, compound

Product 1

HCID 69087691HCID 69087691, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Et3N (36.6 μL, 0.263 mmol) and phenyl isocyanate (10.4 μL, 0.0964 mmol) were added to a solution of tert-butyl (1-{4-[2-(4-aminophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (50.0 mg, 0.0876 mmol) in DCM (1 mL) at 0° C., and stirred at room temperature. After reaction was completed, the mixture was diluted with sat. NaHCO3 and extracted with CHCl3 (3×). The combined organic layers were dried over anhydrous Na2SO4, and concentrated. The residue was purified by PTLC (CHCl3/MeOH=9:1). The fractions were concentrated and solidified with CHCl3. The precipitated solids were collected by filtration and washed with CHCl3 to afford desired product (33.5 mg, 55.4%) as cream colored solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.16-8.11 (m, 1H), 8.03-7.99 (m, 1H), 7.54-7.48 (m, 2H), 7.38-7.21 (m, 9H), 7.16-7.05 (m, 4H), 6.95 (d, J=8.2 Hz, 1H), 6.89-6.73 (m, 3H), 6.59 (dd, J=8.0, 4.8 Hz, 1H), 6.29 (s, 1H), 5.19 (s, 1H), 2.61-2.23 (m, 4H), 2.20-2.06 (m, 1H), 1.95-1.80 (m, 1H), 1.49-1.16 (m, 9H).

Workup

  1. customAfter reaction
  2. extractionextracted with CHCl3 (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by PTLC (CHCl3/MeOH=9:1)
  6. concentrationThe fractions were concentrated
  7. filtrationThe precipitated solids were collected by filtration
  8. washwashed with CHCl3

Sources & evidence

ORD record
ord-1a4407a4c8b94b04953cb7f847042ee5
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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