4-Ethoxy-2-fluoronitrobenzene → (4aS)-3-benzyl-10-ethoxy-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7H)-one

HRID 1035304Notes

Reaction equation

HRID 1035304 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH:12]1CC(O)=O.NC1C=C[C:32]([O:35]CC)=[CH:31]C=1N1CCN(CC2C=CC=CC=2)CC1CC(O)=O.FC1C=C(OCC)C=CC=1[N+]([O-])=O>>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]2[C:3]3[CH:4]=[C:5]([O:8][CH2:9][CH3:10])[CH:6]=[CH:7][C:2]=3[NH:1][C:32](=[O:35])[CH2:31][C@H:12]2[CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 135386514-Ethoxy-2-fluoronitrobenzeneHCID 667696222-(1-(2-amino-5-ethoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid 2-(1-(2-Amino-5-ethoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid

Product 1

HCID 67250321(4aS)-3-benzyl-10-ethoxy-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7H)-one

Procedure

The title compound was prepared according to the procedure outlined in Example 43A substituting 2-(1-(2-amino-5-methoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid for 2-(1-(2-amino-5-ethoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid 2-(1-(2-Amino-5-ethoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid was prepared according the procedure outlined in Examples 12D, 12E, and 12F by substituting 2-fluoro-4-methoxy-1-nitrobenzene with 2-fluoro-4-ethoxy-1-nitrobenzene.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-f72d18e6fa2c4d64a54374f840dfb695
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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