1,4-Dioxane hydrochloride → HCID 56969195, compound

HRID 1047083Notes

Reaction equation

HRID 1047083 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]3[N:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]2[C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2([NH:34]C(=O)OC(C)(C)C)[CH2:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.Cl.O1CCOCC1>ClCCl.C(OCC)C>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]3[N:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]2[C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2([NH2:34])[CH2:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68067420tert-butyl (1-{4-[2-(1,3-thiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

Product 1

HCID 56969195HCID 56969195, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (1-{4-[2-(1,3-thiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (302 mg, 0.54 mmol) and 4N HCl/dioxane (1.5 ml) in dichloromethane (10 ml) was stirred at room temperature for 16 hours and diluted with diethyl ether. The precipitate was collected on a filter paper and dried to give a yellow solid (76%). 1HNMR (DMSO-d6) 400 MHz δ: 8.79 (m, 2H), 8.69 (s, 1H), 8.13 (dd, J=4.9, 1.4 Hz, 1H), 7.93 (dd, J=7.7, 1.4 Hz, 1H), 7.76 (d, J=2.9 Hz, 1H), 7.72 (d, J=2.9 Hz, 1H), 7.56-7.50 (m, 4H), 7.40 (td, J=7.7, 1.7 Hz, 1H), 7.33 (d, J=7.5 Hz, 1H), 7.15 (td, J=7.5, 1.2 Hz, 1H) 6.91 (dd, J=8.0, 1.7 Hz, 1H), 6.76 (dd, J=8.0, 4.6 Hz, 1H), 2.60-2.55 (m, 4H), 2.25-2.15 (m, 1H), 1.86-1.76 (m, 1H); LC/MS [M+H]: 463.

Workup

  1. customThe precipitate was collected on a filter paper
  2. customdried

Sources & evidence

ORD record
ord-eb3a0bac66784c09befa44f606754725
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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