Propane, 1-chloro-3-isocyanato- → HCID 58902299, compound

HRID 1640205Notes

Reaction equation

HRID 1640205 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH:15]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:23]=4)=[O:20])[CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:32][CH2:33][CH2:34][CH2:35][N:36]=[C:37]=[O:38].ClC(C)CN=C=O>C(Cl)Cl>[C:28]([C:24]1[CH:23]=[C:22]([NH:21][C:19]([CH:15]2[CH2:14][CH2:13][C:12]3[C:17](=[CH:18][C:9]([O:8][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:37]([NH:36][CH2:35][CH2:34][CH2:33][Cl:32])=[O:38])[CH:7]=4)=[CH:10][CH:11]=3)[CH2:16]2)=[O:20])[CH:27]=[CH:26][CH:25]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 166752Propane, 1-chloro-3-isocyanato-HCID 19773524HCID 19773524, compoundHCID 58902256HCID 58902256, compound

Product 1

HCID 58902299HCID 58902299, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[(2-aminopyridin-4-yl)oxy]-N-(3-tert-butylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (0.965 g, 2.32 mmol) in DCM (30 mL) was added 3-chloropropyl isocyanate (0.357 mL, 3.48 mmol). The reaction mixture was allowed to stir at rt for 64 hr. Additional 2-chloropropyl isocyanate (0.300 mL, 2.92 mmol) was added, and the reaction mixture was allowed to stir at rt for 24 h. The solvent was evaporated and the residue was purified by column chromatography to give N-(3-tert-butylphenyl)-7-{[2-({[(3-chloropropyl)amino]-carbonyl}amino)pyridin-4-yl]oxy}-1,2,3,4tetrahydronaphthalene-2-carboxamide (0.710 g; 1.33 mmol, 57%) as a white solid. LCMS: (FA) ES+536.6, ES−533.5.

Workup

  1. stirringto stir at rt for 24 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e9ea55a5fcad45c190927137aa23fad1
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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