Ethyl Acetate → {6-(2,4-Dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester

HRID 420534ノート

反応式

HRID 420534 の反応式
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH2:26])=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN([CH:34]([CH3:36])[CH3:35])C(C)C.CN([C:40]([O:44]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCO[C:64]([CH3:66])=[O:65]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH:26][C:40]([CH:35]3[CH2:34][CH2:36][O:65][CH2:64][CH2:66]3)=[O:44])=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57906484[3-Amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 57906481{6-(2,4-Dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a mixture of [3-amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester (100 mg, 0.25 mmol), tetrahydro-pyran-4-arboxylic acid (192 mg, 1.47 mmol) and DIPEA (0.52 mL, 2.95 mmol) in DMF (3 mL) was added HATU (560 mg, 1.47 mmol) at RT. The reaction mixture was heated at 80° C. and stirred for 24 h, then poured into AcOEt (50 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×25 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→84:16) to yield the title compound (79.5 mg, 0.153 mmol, 62%). MS: 519 [M+1]+; HPLC: AtRet=1.49; TLC: RF 0.14 (DCM/MeOH 95:5).

後処理

  1. washwashed with a 2.0 M aqueous Na2CO3 solution (2×25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→84:16)

出典と根拠

ORDレコード
ord-59377f9632604eceaaf9b36c8a2b60da
出典データセット
uspto-grants-2012_01
特許番号
US08097617B2

反応ノート

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