4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 6-Acetyl-9-chloro-3-fluoro-5,6-dihydro-2-[6-(4-morpholinyl)-3-pyridinyl]pyrido[3,2-c][1]benzazocine

HRID 2224313Notes

Reaction equation

HRID 2224313 reaction equation
[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[N:17]=[C:18](Cl)[C:19]([F:21])=[CH:20][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:31]2[CH:32]=[CH:33][C:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[N:35][CH:36]=2)O1.C(N1C2C=CC=CC=2C=CC2N=C(C3C=NC(OC)=CC=3)C(F)=CC=2C1)(=O)C>>[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[N:17]=[C:18]([C:31]3[CH:36]=[N:35][C:34]([N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)=[CH:33][CH:32]=3)[C:19]([F:21])=[CH:20][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 692911976-Acetyl-3-fluoro-5,6-dihydro-2-(6-methoxy-3-pyridinyl)-pyrido[3,2-c][1]benzazocineHCID 723667786-Acetyl-2,9-dichloro-3-fluoro-5,6-dihydropyrido[3,2-c][1]benzazocine

Product 1

HCID 692910616-Acetyl-9-chloro-3-fluoro-5,6-dihydro-2-[6-(4-morpholinyl)-3-pyridinyl]pyrido[3,2-c][1]benzazocineYield 64.5%

Procedure

The title compound (21.6 mg, 64.3%) was prepared from 9C (24.4 mg, 0.072 mmol) and 5A (22 mg, 0.072 mmol) by a route analogous to that used for the preparation of 2B. HPLC Rt=2.649 min; LCMS Found: (M+H)+=465.

Sources & evidence

ORD record
ord-402cf35b95db47629b2bb1ef99c2ccf0
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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