Triethylamine → HCID 69087653, compound

HRID 1047029Notes

Reaction equation

HRID 1047029 reaction equation
CCN(CC)CC.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]4[N:33]=[CH:34][CH:35]=[CH:36][C:24]=4[N:23]3[C:37]=2[C:38]2[CH:43]=[CH:42][C:41]([C:44]3([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:47][CH2:46][CH2:45]3)=[CH:40][CH:39]=2)=[CH:16][CH:15]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:8][S:9]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]4[N:33]=[CH:34][CH:35]=[CH:36][C:24]=4[N:23]3[C:37]=2[C:38]2[CH:43]=[CH:42][C:41]([C:44]3([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:53])([CH3:52])[CH3:54])[CH2:45][CH2:46][CH2:47]3)=[CH:40][CH:39]=2)=[CH:18][CH:19]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69087658HCID 69087658, compound

Product 1

HCID 69087653HCID 69087653, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Et3N (36.6 μL, 0.263 mmol) and methanesulfonyl chloride (7.46 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, CHCl3/EtOAc=1:1) to afford desired product (30.9 mg, 54.4%) as pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.18-8.12 (m, 1H), 8.04-7.97 (m, 1H), 7.63-7.50 (m, 2H), 7.41-7.33 (m, 2H), 7.33-7.23 (m, 2H), 7.19-7.08 (m, 5H), 6.96 (d, J=7.8 Hz, 1H), 6.80 (d, J=7.8 Hz, 1H), 6.60 (dd, J=7.8, 4.6 Hz, 1H), 6.44 (br s, 1H), 5.69-4.98 (m, 1H), 2.98 (s, 3H), 2.63-2.27 (m, 4H), 2.21-2.06 (m, 1H), 1.96-1.82 (m, 1H), 1.38 (br s, 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, CHCl3/EtOAc=1:1)

Sources & evidence

ORD record
ord-6d446905e84646918638e4ea188d8542
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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