(E)-tert-butyl (1-(4-(2-styryl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate → tert-butyl (1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate

HRID 1047091Notes

Reaction equation

HRID 1047091 reaction equation
[CH:1](/[C:9]1[N:10]=[C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:14]3[N:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]2[C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.CO.[Pd]>[C:3]1([CH2:2][CH2:1][C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]4[N:22]=[CH:23][CH:24]=[CH:25][C:13]=4[N:12]3[C:26]=2[C:27]2[CH:28]=[CH:29][C:30]([C:33]3([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[CH2:36][CH2:35][CH2:34]3)=[CH:31][CH:32]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 69087673(E)-tert-butyl (1-(4-(2-styryl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 136331867tert-butyl (1-(4-(2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(E)-tert-butyl (1-(4-(2-styryl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate was stirred in THF-MeOH under hydrogen in the presence of 5% Pd/C to give the title compound 1HNMR (CDCl3) 400 MHz δ: 8.10 (dd, J=7.7, 1.4 Hz, 1H), 7.99 (dd, J=4.6, 1.2 Hz, 1H), 7.34-7.27 (m, 3H), 7.24 (d, J=6.9 Hz, 1H), 7.18 (d, J=7.5 Hz, 2H), 7.14 (td, J=7.5, 1.2 Hz, 1H), 6.95 (d, J=7.5 Hz, 1H), 6.90 (d, J=7.5 Hz, 2H), 6.78 (d, J=7.5 Hz, 1H), 6.59 (dd, J=8.0, 4.6 Hz, 1H), 6.29 (s, 1H), 5.08 (s, 1H), 3.12-3.07 (m, 2H), 3.01-2.95 (m, 2H), 2.56-2.38 (m, 4H), 2.16-2.07 (m, 1H), 1.91-1.82 (m, 1H), 1.48-1.19 (m, 9H); LC/MS [M+H]: 584.

Sources & evidence

ORD record
ord-e9dcb9442bce4475bc2e8e79fcd9e49c
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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