Hydrochloric Acid → HCID 67503142, compound

HRID 1047035Notes

Reaction equation

HRID 1047035 reaction equation
[CH3:1][C:2]([NH:34]C(=O)OC(C)(C)C)([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]3[C:15]4[CH:27]=[CH:26][CH:25]=[N:24][C:16]=4[NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:13]3=[N:12][C:11]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][CH:5]=1)[CH3:3].[ClH:42]>ClCCl.O1CCOCC1>[ClH:42].[C:28]1([C:11]2[N:12]=[C:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[NH:17][C:16]4[N:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]3[C:10]=2[C:7]2[CH:6]=[CH:5][C:4]([C:2]([NH2:34])([CH3:1])[CH3:3])=[CH:9][CH:8]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69087668tert-butyl {1-methyl-1-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl) phenyl]ethyl}carbamate

Product 1

HCID 67503142HCID 67503142, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl {1-methyl-1-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]ethyl}carbamate (41 mg) in dichloromethane (4 mL) was added hydrogen chloride in 1,4-dioxane (2.5 mL) dropwise at room temperature. After being stirred at the same temperature for 5 h, the reaction mixture was concentrated under reduced pressure. The residue was suspended with ethyl acetate and filtered to give the product (37 mg, 85%). 1HNMR (DMSO-d6) 400 MHz δ: 8.72-8.62 (m, 3H), 8.11 (dd, J=4.6, 1.8 Hz, 1H), 7.96 (dd, J=7.8, 1.4 Hz, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.52-7.47 (m, 2H), 7.42-7.25 (m, 7H), 7.17-7.11 (m, 1H), 6.88 (dd, J=8.0, 1.8 Hz, 1H), 6.74 (dd, J=8.0, 4.6 Hz, 1H), 1.63 (s, 6H). LCMS: 444 [M+H].

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered

Sources & evidence

ORD record
ord-6733c72e5fda45359ff934bc20f40c2b
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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