Trifluoroacetic acid → 3-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-amine

HRID 1047042Notes

Reaction equation

HRID 1047042 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]4[N:20]=[CH:21][CH:22]=[CH:23][C:11]=4[N:10]3[C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([C:31]3([NH:35]C(=O)OC(C)(C)C)[CH2:34][O:33][CH2:32]3)=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([C:7]2[N:8]=[C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]4[N:20]=[CH:21][CH:22]=[CH:23][C:11]=4[N:10]3[C:24]=2[C:25]2[CH:26]=[CH:27][C:28]([C:31]3([NH2:35])[CH2:32][O:33][CH2:34]3)=[CH:29][CH:30]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69087676tert-butyl {3-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-yl}carbamate

Product 1

HCID 569689643-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl {3-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]oxetan-3-yl}carbamate (29 mg) in dichloromethane (4 mL) was added trifluoroacetic acid (2 mL) at 0° C. dropwise. After being stirred at room temperature for 1 h, the reaction mixture was concentrated under reduced pressure. Purification by column chromatography (NH-silica gel: 0-3% methanol in chloroform) gave the product (16 mg, 68%). 1HNMR (DMSO-d6) 400 MHz δ: 8.57 (s, 1H), 8.08 (dd, J=4.8, 1.6 Hz, 1H), 7.96 (dd, J=7.8, 1.4 Hz, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.53-7.49 (m, 2H), 7.38-7.21 (m, 7H), 7.12 (t, J=7.6 Hz, 1H), 6.90 (dd, J=8.0, 1.6 Hz), 6.74 (dd, J=8.0, 4.8 Hz, 1H), 4.71-4.65 (m, 4H). LCMS: 458 [M+H].

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customPurification by column chromatography (NH-silica gel: 0-3% methanol in chloroform)

Sources & evidence

ORD record
ord-43e0202239404a6b83fe5e2b72c7c073
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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