Acetic Anhydride → HCID 69087652, compound

HRID 1047013Notes

Reaction equation

HRID 1047013 reaction equation
CCN(CC)CC.[CH3:8][C:9](OC(C)=O)=[O:10].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[NH:28][C:27]4[N:35]=[CH:36][CH:37]=[CH:38][C:26]=4[N:25]3[C:39]=2[C:40]2[CH:45]=[CH:44][C:43]([C:46]3([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:49][CH2:48][CH2:47]3)=[CH:42][CH:41]=2)=[CH:18][CH:17]=1>C(Cl)Cl>[C:9]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:23]=[C:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[NH:28][C:27]4[N:35]=[CH:36][CH:37]=[CH:38][C:26]=4[N:25]3[C:39]=2[C:40]2[CH:45]=[CH:44][C:43]([C:46]3([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:56])[CH3:55])[CH2:47][CH2:48][CH2:49]3)=[CH:42][CH:41]=2)=[CH:20][CH:21]=1)(=[O:10])[CH3:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69087658HCID 69087658, compound

Product 1

HCID 69087652HCID 69087652, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (25.9 μL, 0.186 mmol) and Ac2O (6.45 μL, 0.0682 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 (35.4 mg, 0.0620 mmol) in DCM (1 mL) at 0° C. After stiffing the mixture for 17.5 hours at room temperature, the mixture was concentrated. The residue was diluted with sat. NaHCO3 aq. 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) to afford desired product (22.6 mg, 59.5%) as a white solid. 1HNMR (CDCl3) 400 MHz δ: 8.18-8.13 (m, 1H), 8.03-7.97 (m, 1H), 7.60-7.49 (m, 2H), 7.45-7.25 (m, 8H), 7.19-7.10 (m, 3H), 6.95 (d, J=7.8 Hz, 1H), 6.85-6.73 (m, 1H), 6.59 (dd, J=8.0, 4.8 Hz, 1H), 6.46-6.37 (m, 1H), 5.27-5.17 (m, 1H), 2.64-2.25 (m, 4H), 2.20-2.01 (m, 1H), 2.14 (s, 3H), 1.98-1.83 (m, 1H), 1.38 (br s, 9H); LCMS: 613 [M+H].

Workup

  1. customfor 17.5 hours
  2. customat room temperature
  3. concentrationthe mixture was concentrated
  4. additionThe residue was diluted with sat. NaHCO3 aq.
  5. extractionextracted with CHCl3 (3×)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by PTLC (CHCl3/MeOH=9:1)

Sources & evidence

ORD record
ord-49d971d321864718b76aa3e7506ca513
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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