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Diisopropylcarbodiimide → 1-(4-(2-(4-Chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl)-2-methoxyphenoxy)-2-methylpropan-2-yl 2-(tert-butoxycarbonylamino)acetate

HRID 2263662
Notes
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Reaction equation

HRID 2263662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:31][C:11]3[C:12](=[O:30])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])=[C:18]([O:28][CH3:29])[CH:17]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[C:32]([NH:39][CH2:40][C:41](O)=[O:42])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(N=C=NC(C)C)(C)C>C(Cl)Cl>[C:35]([O:34][C:32]([NH:39][CH2:40][C:41]([O:27][C:24]([CH3:26])([CH3:25])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[C:12](=[O:30])[C:11]3[S:31][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)=[CH:9][C:10]=3[CH:15]=[N:14]2)=[CH:17][C:18]=1[O:28][CH3:29])=[O:42])=[O:33])([CH3:38])([CH3:37])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 251172722-(4-chlorophenyl)-6-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)thieno[2,3-d]pyridazin-7(6H)-one

Product 1

HCID 251172741-(4-(2-(4-Chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl)-2-methoxyphenoxy)-2-methylpropan-2-yl 2-(tert-butoxycarbonylamino)acetate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 2-(4-chlorophenyl)-6-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)thieno[2,3-d]pyridazin-7(6H)-one (100 mg, 0.219 mmol) that was prepared in Example 9,4-(pyrrolidin-1-yl)pyridine (32.4 mg, 0.219 mmol) and boc-glycine (192 mg, 1.094 mmol) in CH2Cl2 (10 ml) was added N,N′-diisopropylcarbodiimide (0.170 ml, 1.094 mmol). The mixture was stirred at reflux for 1 hours and then at RT for 18 hours. LC-MS analysis revealed desired product as well as the imide resulting from condensation with a second Boc-glycine. The later product was cleaved to regenerate desired product by addition of hydrazine (0.343 ml, 10.94 mmol) was added and the stirring at RT for 30 min. The reaction was diluted with a solution of saturated NaHCO3 (15 ml) and extracted with CH2Cl2 (20 ml). The CH2Cl2 extracts were dried over Na2SO4 and concentrated. The crude product was purified by ISCO chromatography on two silica gel column (2×12 g) employing a 10 min gradient ranging from hexane to 100% ethyl acetate to elute 1-(4-(2-(4-chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl)-2-methoxyphenoxy)-2-methylpropan-2-yl 2-(tert-butoxycarbonylamino)acetate (130 mg, 0.212 mmol, 97% yield) as light brown solid.

Workup

  1. temperatureat reflux for 1 hours

Sources & evidence

ORD record
ord-9871827d281241efbe5dc4fc67c8a995
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851622B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes