Chloride → HCID 86613296, compound

HRID 1640212Notes

Reaction equation

HRID 1640212 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-].O.[CH2:34]1[CH2:38]O[CH2:36][CH2:35]1>>[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][CH2:23][CH:22]([N:21]5[CH2:38][CH2:34][CH2:35][CH2:36]5)[CH3:27])[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 4

HCID 312ChlorideHCID 962WaterHCID 8028TetrahydrofuranHCID 58902256HCID 58902256, compound

Product 1

HCID 86613296HCID 86613296, compound

Procedure

To a solution of 7-[(2-aminopyridin-4-yl)oxy]-N-(3-tert-butylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (1.50 g, 3.64 mmol) in THF (36 mL) at 0°, was added TEA (1.02 mL, 7.29 mmol) and then 2-chloropropanyoyl chloride (0.39 mL, 4.01 mmol) dropwise. The reaction was allowed to warm to rt and stir for 18 h. Water was added and the mixture was extracted with EtOAc (2×). The organic solutions were combined, washed with water, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give N-(3tert-butylphenyl)-7-({2-[(2-pyrrolidin-1-ylpropanyl)amino]pyridin-4yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxamide I-275 as a pale yellow solid (1.37 g, 74.9%).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0b6aba6f6d774cb287930a29866d60b3
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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