7-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one → 3-[6'-benzyloxy-4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetra-hydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469360Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.[CH2:21]([O:28][C:29]1[CH:34]=[C:33]([C:35]([C:37]2[CH:47]=[C:46]([CH3:48])[C:40]3[N:41]([CH3:45])[C:42](=[O:44])[O:43][C:39]=3[CH:38]=2)=[O:36])[CH:32]=[C:31](Cl)[N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN1C(=O)CCC1>[CH2:21]([O:28][C:29]1[N:30]=[C:31]([N:17]2[CH2:18][CH2:19][CH:14]([N:10]3[CH2:9][CH2:8][C:7]4[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[NH:12][C:11]3=[O:13])[CH2:15][CH2:16]2)[CH:32]=[C:33]([C:35]([C:37]2[CH:47]=[C:46]([CH3:48])[C:40]3[N:41]([CH3:45])[C:42](=[O:44])[O:43][C:39]=3[CH:38]=2)=[O:36])[CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

991 mg (3.60 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 500 mg (1.22 mmol) 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one were combined in 10 mL NMP and stirred overnight at 120° C. The reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were combined and evaporated down.

Workup

customThe reaction mixture was purified by preparative HPLC-MS
additionThe fractions containing the product
customevaporated down

Sources & evidence

ORD record: ord-a24ac539a47943eaa52dc104de08a810
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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