HCID 70654479, compound → HCID 70654759, compound

HRID 2091571Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:8][NH:7][C:6]2[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:11]=[CH:12][C:5]=2[C:4](=[O:22])[NH:3]1.[NH2:23][C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH:39][CH:40]3[CH2:42][CH2:41]3)(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:26][C:25]=1Br>>[NH2:23][C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([S:36]([NH:39][CH:40]3[CH2:42][CH2:41]3)(=[O:37])=[O:38])=[CH:34][CH:35]=2)=[CH:26][C:25]=1[C:10]1[CH:11]=[CH:12][C:5]2[C:4](=[O:22])[NH:3][C@@H:2]([CH3:1])[CH2:8][NH:7][C:6]=2[CH:9]=1

Participants

Reactant 2

HCID 70654479HCID 70654479, compound

HCID 70654595HCID 70654595, compound

Product 1

HCID 70654759HCID 70654759, compoundYield 33%

Procedure

General method C was applied to (S)-3-methyl-8-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (303 mg, 0.7 mmol) and 4-(6-amino-5-bromopyridin-3-yl)-N-cyclopropylbenzenesulfonamide to give (S)-4-(6-amino-5-(3-methyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-yl)pyridin-3-yl)-N-cyclopropylbenzenesulfonamide as a yellow solid (180 mg, 33% yield) after purification by reverse phase preparatory HPLC. MS (EI) m/z=464.6 [M+1]+.

Sources & evidence

ORD record: ord-7771220146db4efc833b5c79c9616d2c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440652B2

Reaction notes

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