HCID 19082048, compound → HCID 66706661, compound

HRID 911564Notes

Reaction equation

HRID 911564 reaction equation
Cl[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([C:27]#[CH:28])=[C:23]([Cl:26])[CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([C:27]#[C:28][N:2]3[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]3)=[C:23]([Cl:26])[CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 19082048HCID 19082048, compoundHCID 59787377HCID 59787377, compound

Product 1

HCID 66706661HCID 66706661, compoundYield 19.8%

Procedure

Use a method similar to the General Procedure 8 to couple 2-chloro-pyridazine (98 mg, 0.86 mmol) with 3-tert-butoxycarbonyl-7-chloro-6-ethynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (104 mg, 0.34 mmol). Purify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 30 min) to give 3-tert-butoxycarbonyl-7-chloro-6-pyridazin-2-ylethynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (26 mg, 10%). MS (ES+) m/z: 384 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 30 min)

Sources & evidence

ORD record
ord-f3d5183442b74ae6b391c9e36f613aee
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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