Tert-Butylamine → N-tert-Butyl-6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinamide

HRID 408878ノート

反応式

HRID 408878 の反応式
[CH:1]1([NH:5][C:6](=[O:33])[NH:7][C:8]2[CH:31]=[CH:30][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[N:26]=[C:25]([C:27]([O-:29])=O)[CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:32])[CH2:4][CH2:3][CH2:2]1.[Na+].C(N(CC)CC)C.[C:42]([NH2:46])([CH3:45])([CH3:44])[CH3:43].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[C:42]([NH:46][C:27](=[O:29])[C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:20][N:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C:11]3[CH:30]=[CH:31][C:8]([NH:7][C:6]([NH:5][CH:1]4[CH2:4][CH2:3][CH2:2]4)=[O:33])=[C:9]([F:32])[CH:10]=3)[CH2:15][CH2:16]2)[N:26]=1)([CH3:45])([CH3:44])[CH3:43]

参加物

6

反応物 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 66661327Sodium 6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinate

生成物 1

HCID 46182303N-tert-Butyl-6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinamide収率 22.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium 6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)-picolinate (100 mg, 0.209 mmol), triethylamine (66 mg, 0.693 mmol, 0.091 mL) and tert-butylamine (32 mg, 0.435 mmol) were combined and stirred at room temperature in dichloromethane. 1-Propanephosphonic acid cyclic anhydride (208 mg, 0.326 mmol, 0.194 mL, 50% solution in ethyl acetate) was added dropwise and the reaction allowed to stir for 1 hour. The reaction mixture was concentrated at reduced pressure, the resulting residue taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated under vacuum to afford the title compound (24 mg). MS (ESI) m/z 511.6 [M+H]+

後処理

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-4a47a204cc7e4ab2b1656a16b64f2ac7
出典データセット
uspto-grants-2014_06
特許番号
US08759352B2

反応ノート

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